# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_6DipCl2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H43 Cl2 N2'
_chemical_formula_weight         514.57

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   20.472(4)
_cell_length_b                   14.638(3)
_cell_length_c                   21.347(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.09(3)
_cell_angle_gamma                90.00
_cell_volume                     5793(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2216
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   XDS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71080
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Australian Synchrotron'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23208
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5092
_reflns_number_gt                4520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu-Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CifTAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 A molecule of benzene was located in the asymmetric unit and its atomic
 positions refined isotropically at 5o% occupancy.
 The high r-factors for the crystal structure is due to weak reflection data
 above theta angle of 23 deg. This also partially gives rise to the low data 
 completeness for the structure.
 The low value (94.3%) for completeness of data to theta = 25.5 deg. also arises 
 from hardware constraints associated with the diffractometer used at the 
 Australian Synchrotron and is common for data sets on that instrument. 
 Its minimum crystal to detector distance is 72 mm and its
 goniometer only rotates about the phi axis. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1266P)²+34.4121P] where P=(Fo²+2Fc²)/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         5092
_refine_ls_number_parameters     321
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0910
_refine_ls_wR_factor_ref         0.2531
_refine_ls_wR_factor_gt          0.2475
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25402(6) 0.87002(7) 0.00823(6) 0.0417(3) Uani 1 1 d . . .
Cl2 Cl 0.37803(6) 1.02158(10) 0.27732(5) 0.0519(4) Uani 1 1 d . . .
N2 N 0.38241(15) 0.91037(18) 0.10300(14) 0.0204(6) Uani 1 1 d . . .
N1 N 0.29952(17) 1.0295(2) 0.06404(15) 0.0256(7) Uani 1 1 d . . .
C5 C 0.39978(19) 0.8146(2) 0.10081(17) 0.0216(7) Uani 1 1 d . . .
C17 C 0.2271(2) 1.0616(2) 0.02346(19) 0.0294(9) Uani 1 1 d . . .
C2 C 0.3525(2) 1.0974(2) 0.11008(19) 0.0302(8) Uani 1 1 d . . .
H2A H 0.3471 1.1032 0.1539 0.036 Uiso 1 1 calc R . .
H2B H 0.3433 1.1579 0.0873 0.036 Uiso 1 1 calc R . .
C18 C 0.1772(2) 1.0560(3) 0.0518(2) 0.0340(9) Uani 1 1 d . . .
C22 C 0.2118(2) 1.0997(3) -0.04186(19) 0.0309(9) Uani 1 1 d . . .
C6 C 0.4320(2) 0.7889(3) 0.05749(18) 0.0257(8) Uani 1 1 d . . .
C4 C 0.4399(2) 0.9700(2) 0.15241(18) 0.0259(8) Uani 1 1 d . . .
H4A H 0.4878 0.9482 0.1578 0.031 Uiso 1 1 calc R . .
H4B H 0.4388 0.9679 0.1983 0.031 Uiso 1 1 calc R . .
C11 C 0.3541(2) 0.7842(3) 0.19372(19) 0.0304(8) Uani 1 1 d . . .
H11 H 0.3460 0.8517 0.1884 0.037 Uiso 1 1 calc R . .
C3 C 0.4277(2) 1.0667(2) 0.12514(19) 0.0293(8) Uani 1 1 d . . .
H3A H 0.4630 1.1079 0.1598 0.035 Uiso 1 1 calc R . .
H3B H 0.4352 1.0698 0.0823 0.035 Uiso 1 1 calc R . .
C23 C 0.2667(2) 1.1023(3) -0.0721(2) 0.0347(9) Uani 1 1 d . . .
H23 H 0.3147 1.0853 -0.0346 0.042 Uiso 1 1 calc R . .
C7 C 0.4484(2) 0.6966(3) 0.0571(2) 0.0326(9) Uani 1 1 d . . .
H7 H 0.4700 0.6762 0.0280 0.039 Uiso 1 1 calc R . .
C10 C 0.3856(2) 0.7538(2) 0.14416(18) 0.0249(8) Uani 1 1 d . . .
C14 C 0.4495(2) 0.8574(3) 0.0133(2) 0.0318(9) Uani 1 1 d . . .
H14 H 0.4260 0.9166 0.0150 0.038 Uiso 1 1 calc R . .
C8 C 0.4339(2) 0.6341(3) 0.0981(2) 0.0359(9) Uani 1 1 d . . .
H8 H 0.4448 0.5714 0.0963 0.043 Uiso 1 1 calc R . .
C9 C 0.4038(2) 0.6621(3) 0.1415(2) 0.0320(9) Uani 1 1 d . . .
H9 H 0.3951 0.6186 0.1701 0.038 Uiso 1 1 calc R . .
C13 C 0.2819(2) 0.7388(3) 0.1768(2) 0.0431(10) Uani 1 1 d . . .
H13A H 0.2885 0.6725 0.1823 0.065 Uiso 1 1 calc R . .
H13B H 0.2485 0.7529 0.1290 0.065 Uiso 1 1 calc R . .
H13C H 0.2620 0.7616 0.2083 0.065 Uiso 1 1 calc R . .
C20 C 0.0912(2) 1.1293(3) -0.0519(2) 0.0440(12) Uani 1 1 d . . .
H20 H 0.0443 1.1534 -0.0778 0.053 Uiso 1 1 calc R . .
C19 C 0.1078(2) 1.0910(3) 0.0119(2) 0.0416(11) Uani 1 1 d . . .
H19 H 0.0721 1.0882 0.0292 0.050 Uiso 1 1 calc R . .
C21 C 0.1417(2) 1.1334(3) -0.0789(2) 0.0405(11) Uani 1 1 d . . .
H21 H 0.1286 1.1594 -0.1234 0.049 Uiso 1 1 calc R . .
C15 C 0.4204(3) 0.8279(4) -0.0624(2) 0.0458(11) Uani 1 1 d . . .
H15A H 0.4446 0.7715 -0.0658 0.069 Uiso 1 1 calc R . .
H15B H 0.4297 0.8761 -0.0894 0.069 Uiso 1 1 calc R . .
H15C H 0.3684 0.8172 -0.0805 0.069 Uiso 1 1 calc R . .
C16 C 0.5311(3) 0.8740(4) 0.0432(2) 0.0465(12) Uani 1 1 d . . .
H16A H 0.5486 0.8946 0.0912 0.070 Uiso 1 1 calc R . .
H16B H 0.5413 0.9208 0.0157 0.070 Uiso 1 1 calc R . .
H16C H 0.5555 0.8170 0.0416 0.070 Uiso 1 1 calc R . .
C26 C 0.1939(2) 1.0140(3) 0.1218(2) 0.0378(10) Uani 1 1 d . . .
H26 H 0.2456 0.9945 0.1424 0.045 Uiso 1 1 calc R . .
C12 C 0.4069(2) 0.7651(3) 0.2688(2) 0.0397(10) Uani 1 1 d . . .
H12A H 0.4152 0.6992 0.2755 0.060 Uiso 1 1 calc R . .
H12B H 0.3866 0.7878 0.3000 0.060 Uiso 1 1 calc R . .
H12C H 0.4527 0.7961 0.2791 0.060 Uiso 1 1 calc R . .
C24 C 0.2735(3) 1.1968(3) -0.0982(3) 0.0476(12) Uani 1 1 d . . .
H24A H 0.2264 1.2163 -0.1334 0.071 Uiso 1 1 calc R . .
H24B H 0.3084 1.1949 -0.1185 0.071 Uiso 1 1 calc R . .
H24C H 0.2901 1.2401 -0.0596 0.071 Uiso 1 1 calc R . .
C27 C 0.1845(3) 1.0832(4) 0.1711(2) 0.0508(13) Uani 1 1 d . . .
H27A H 0.2132 1.1378 0.1739 0.076 Uiso 1 1 calc R . .
H27B H 0.2006 1.0559 0.2172 0.076 Uiso 1 1 calc R . .
H27C H 0.1335 1.1001 0.1538 0.076 Uiso 1 1 calc R . .
C25 C 0.2475(3) 1.0316(4) -0.1302(3) 0.0565(14) Uani 1 1 d . . .
H25A H 0.1999 1.0456 -0.1670 0.085 Uiso 1 1 calc R . .
H25B H 0.2468 0.9705 -0.1118 0.085 Uiso 1 1 calc R . .
H25C H 0.2836 1.0335 -0.1490 0.085 Uiso 1 1 calc R . .
C28 C 0.1479(3) 0.9290(4) 0.1150(3) 0.0559(13) Uani 1 1 d . . .
H28A H 0.0978 0.9473 0.1020 0.084 Uiso 1 1 calc R . .
H28B H 0.1663 0.8965 0.1594 0.084 Uiso 1 1 calc R . .
H28C H 0.1501 0.8886 0.0793 0.084 Uiso 1 1 calc R . .
C1 C 0.31803(19) 0.9431(2) 0.06398(17) 0.0225(7) Uani 1 1 d . . .
C29 C 0.0088(5) 0.9360(4) 0.2462(6) 0.044(2) Uiso 0.50 1 d PD A -1
H29 H 0.0248 0.9953 0.2412 0.053 Uiso 0.50 1 calc PR A -1
C32 C -0.0399(5) 0.7598(5) 0.2612(5) 0.046(2) Uiso 0.50 1 d PD A -1
H32 H -0.0559 0.7003 0.2661 0.055 Uiso 0.50 1 calc PR A -1
C33 C -0.0721(5) 0.8366(5) 0.2736(5) 0.053(2) Uiso 0.50 1 d PD A -1
H33 H -0.1114 0.8303 0.2859 0.064 Uiso 0.50 1 calc PR A -1
C34 C -0.0468(5) 0.9235(5) 0.2679(6) 0.063(3) Uiso 0.50 1 d PD A -1
H34 H -0.0676 0.9755 0.2790 0.076 Uiso 0.50 1 calc PR A -1
C30 C 0.0393(4) 0.8574(5) 0.2324(5) 0.058(3) Uiso 0.50 1 d PD A -1
H30 H 0.0761 0.8629 0.2165 0.070 Uiso 0.50 1 calc PR A -1
C31 C 0.0161(4) 0.7713(4) 0.2417(5) 0.037(2) Uiso 0.50 1 d PD A -1
H31 H 0.0394 0.7188 0.2345 0.045 Uiso 0.50 1 calc PR A -1


_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
Cl1 C1 1.719(4) . ?
N2 C1 1.315(5) . ?
N2 C5 1.451(4) . ?
N2 C4 1.485(4) . ?
N1 C1 1.321(4) . ?
N1 C17 1.442(5) . ?
N1 C2 1.492(4) . ?
C5 C6 1.396(5) . ?
C5 C10 1.400(5) . ?
C17 C18 1.393(6) . ?
C17 C22 1.408(6) . ?
C2 C3 1.502(6) . ?
C18 C19 1.407(6) . ?
C18 C26 1.514(6) . ?
C22 C21 1.402(6) . ?
C22 C23 1.516(6) . ?
C6 C7 1.392(5) . ?
C6 C14 1.521(5) . ?
C4 C3 1.510(5) . ?
C11 C13 1.518(6) . ?
C11 C10 1.522(5) . ?
C11 C12 1.533(6) . ?
C23 C24 1.520(6) . ?
C23 C25 1.533(6) . ?
C7 C8 1.384(6) . ?
C10 C9 1.399(5) . ?
C14 C15 1.528(6) . ?
C14 C16 1.533(6) . ?
C8 C9 1.375(6) . ?
C20 C19 1.376(7) . ?
C20 C21 1.382(7) . ?
C26 C28 1.531(7) . ?
C26 C27 1.532(6) . ?
C29 C30 1.399(6) . ?
C29 C34 1.412(7) . ?
C32 C33 1.385(6) . ?
C32 C31 1.388(7) . ?
C33 C34 1.397(6) . ?
C30 C31 1.390(6) . ?

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
C1 N2 C5 121.6(3) . . ?
C1 N2 C4 121.0(3) . . ?
C5 N2 C4 117.3(3) . . ?
C1 N1 C17 122.3(3) . . ?
C1 N1 C2 120.6(3) . . ?
C17 N1 C2 117.0(3) . . ?
C6 C5 C10 123.6(3) . . ?
C6 C5 N2 118.3(3) . . ?
C10 C5 N2 118.1(3) . . ?
C18 C17 C22 123.9(4) . . ?
C18 C17 N1 118.4(3) . . ?
C22 C17 N1 117.6(4) . . ?
N1 C2 C3 109.6(3) . . ?
C17 C18 C19 117.0(4) . . ?
C17 C18 C26 123.5(4) . . ?
C19 C18 C26 119.5(4) . . ?
C21 C22 C17 116.3(4) . . ?
C21 C22 C23 121.2(4) . . ?
C17 C22 C23 122.5(3) . . ?
C7 C6 C5 116.7(3) . . ?
C7 C6 C14 120.9(3) . . ?
C5 C6 C14 122.3(3) . . ?
N2 C4 C3 109.0(3) . . ?
C13 C11 C10 111.4(3) . . ?
C13 C11 C12 110.7(3) . . ?
C10 C11 C12 110.8(3) . . ?
C2 C3 C4 110.5(3) . . ?
C22 C23 C24 112.2(3) . . ?
C22 C23 C25 110.3(4) . . ?
C24 C23 C25 110.4(4) . . ?
C8 C7 C6 121.3(4) . . ?
C9 C10 C5 116.8(3) . . ?
C9 C10 C11 120.5(3) . . ?
C5 C10 C11 122.8(3) . . ?
C6 C14 C15 112.4(3) . . ?
C6 C14 C16 110.4(3) . . ?
C15 C14 C16 110.6(3) . . ?
C9 C8 C7 120.5(4) . . ?
C8 C9 C10 121.0(4) . . ?
C19 C20 C21 121.1(4) . . ?
C20 C19 C18 120.6(4) . . ?
C20 C21 C22 121.1(4) . . ?
C18 C26 C28 111.4(4) . . ?
C18 C26 C27 111.6(4) . . ?
C28 C26 C27 110.5(4) . . ?
N2 C1 N1 124.0(3) . . ?
N2 C1 Cl1 118.5(3) . . ?
N1 C1 Cl1 117.5(3) . . ?
C30 C29 C34 117.2(5) . . ?
C33 C32 C31 118.6(5) . . ?
C32 C33 C34 119.9(5) . . ?
C33 C34 C29 121.8(5) . . ?
C31 C30 C29 120.3(5) . . ?
C32 C31 C30 122.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         1.948
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 1012341'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6DipGeCl2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H48 Cl2 Ge N2'
_chemical_formula_weight         640.24

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ge Ge 0.1547 1.8001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.9126(3)
_cell_length_b                   14.6493(4)
_cell_length_c                   22.7915(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3309.61(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_process_details   'SCALE3 ABSPACK'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23126
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7587
_reflns_number_gt                7155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 A molecule of toluene of crystallisation was located in the asymmetric
 unit and its carbon atoms were refined anisotropically. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0258P)²+0.5364P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(5)
_refine_ls_number_reflns         7587
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0546
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Ge1 Ge 0.178417(18) 0.397950(11) 0.204987(7) 0.01653(5) Uani 1 1 d . . .
Cl1 Cl 0.31802(5) 0.27444(3) 0.20007(2) 0.03726(12) Uani 1 1 d . . .
N1 N 0.30725(14) 0.47486(9) 0.32509(5) 0.0143(3) Uani 1 1 d . . .
C1 C 0.31349(17) 0.46724(9) 0.26658(6) 0.0125(3) Uani 1 1 d . . .
Cl2 Cl 0.02520(4) 0.32860(3) 0.264620(16) 0.01874(8) Uani 1 1 d . . .
N2 N 0.41118(14) 0.51237(9) 0.23804(5) 0.0149(3) Uani 1 1 d . . .
C2 C 0.40624(18) 0.52643(12) 0.36115(7) 0.0207(4) Uani 1 1 d . . .
H2A H 0.4230 0.4932 0.3983 0.025 Uiso 1 1 calc R . .
H2B H 0.3685 0.5871 0.3710 0.025 Uiso 1 1 calc R . .
C3 C 0.53778(19) 0.53846(13) 0.32855(7) 0.0230(4) Uani 1 1 d . . .
H3A H 0.5967 0.5818 0.3499 0.028 Uiso 1 1 calc R . .
H3B H 0.5853 0.4792 0.3255 0.028 Uiso 1 1 calc R . .
C4 C 0.50646(19) 0.57477(12) 0.26820(7) 0.0228(4) Uani 1 1 d . . .
H4A H 0.4660 0.6364 0.2714 0.027 Uiso 1 1 calc R . .
H4B H 0.5907 0.5799 0.2451 0.027 Uiso 1 1 calc R . .
C5 C 0.19374(17) 0.44074(10) 0.35895(6) 0.0145(3) Uani 1 1 d . . .
C6 C 0.20719(17) 0.35726(11) 0.38873(6) 0.0163(3) Uani 1 1 d . . .
C7 C 0.09661(18) 0.32663(11) 0.42103(7) 0.0189(3) Uani 1 1 d . . .
H7 H 0.1026 0.2704 0.4417 0.023 Uiso 1 1 calc R . .
C8 C -0.02162(19) 0.37664(11) 0.42355(7) 0.0205(4) Uani 1 1 d . . .
H8 H -0.0968 0.3538 0.4448 0.025 Uiso 1 1 calc R . .
C9 C -0.03043(18) 0.45984(11) 0.39521(7) 0.0190(3) Uani 1 1 d . . .
H9 H -0.1117 0.4940 0.3976 0.023 Uiso 1 1 calc R . .
C10 C 0.07798(17) 0.49444(10) 0.36318(6) 0.0158(3) Uani 1 1 d . . .
C11 C 0.33471(19) 0.29905(11) 0.38679(7) 0.0196(3) Uani 1 1 d . . .
H11 H 0.4018 0.3303 0.3609 0.023 Uiso 1 1 calc R . .
C12 C 0.3060(2) 0.20473(12) 0.36103(8) 0.0276(4) Uani 1 1 d . . .
H12A H 0.2413 0.1725 0.3861 0.041 Uiso 1 1 calc R . .
H12B H 0.3901 0.1697 0.3589 0.041 Uiso 1 1 calc R . .
H12C H 0.2681 0.2115 0.3215 0.041 Uiso 1 1 calc R . .
C13 C 0.3965(2) 0.29026(14) 0.44836(8) 0.0321(5) Uani 1 1 d . . .
H13A H 0.3324 0.2593 0.4744 0.048 Uiso 1 1 calc R . .
H13B H 0.4164 0.3512 0.4639 0.048 Uiso 1 1 calc R . .
H13C H 0.4800 0.2546 0.4461 0.048 Uiso 1 1 calc R . .
C14 C 0.06341(18) 0.58789(11) 0.33384(7) 0.0196(3) Uani 1 1 d . . .
H14 H 0.1508 0.6025 0.3141 0.024 Uiso 1 1 calc R . .
C15 C -0.0465(2) 0.58556(12) 0.28681(8) 0.0284(4) Uani 1 1 d . . .
H15A H -0.0239 0.5393 0.2573 0.043 Uiso 1 1 calc R . .
H15B H -0.0528 0.6455 0.2680 0.043 Uiso 1 1 calc R . .
H15C H -0.1332 0.5703 0.3050 0.043 Uiso 1 1 calc R . .
C16 C 0.0356(2) 0.66289(12) 0.37918(8) 0.0299(4) Uani 1 1 d . . .
H16A H -0.0517 0.6517 0.3980 0.045 Uiso 1 1 calc R . .
H16B H 0.0340 0.7224 0.3596 0.045 Uiso 1 1 calc R . .
H16C H 0.1069 0.6625 0.4090 0.045 Uiso 1 1 calc R . .
C17 C 0.42028(17) 0.51048(11) 0.17440(6) 0.0144(3) Uani 1 1 d . . .
C18 C 0.51769(18) 0.45406(10) 0.14793(7) 0.0164(3) Uani 1 1 d . . .
C19 C 0.52079(18) 0.45162(11) 0.08684(7) 0.0198(3) Uani 1 1 d . . .
H19 H 0.5830 0.4124 0.0676 0.024 Uiso 1 1 calc R . .
C20 C 0.43477(19) 0.50541(12) 0.05351(7) 0.0212(4) Uani 1 1 d . . .
H20 H 0.4369 0.5016 0.0119 0.025 Uiso 1 1 calc R . .
C21 C 0.34600(18) 0.56458(12) 0.08081(7) 0.0201(4) Uani 1 1 d . . .
H21 H 0.2904 0.6031 0.0575 0.024 Uiso 1 1 calc R . .
C22 C 0.33648(17) 0.56891(10) 0.14177(6) 0.0158(3) Uani 1 1 d . . .
C23 C 0.62558(18) 0.40307(12) 0.18221(7) 0.0221(3) Uani 1 1 d . . .
H23 H 0.5969 0.3992 0.2242 0.026 Uiso 1 1 calc R . .
C24 C 0.6541(2) 0.30650(12) 0.15977(8) 0.0280(4) Uani 1 1 d . . .
H24A H 0.5689 0.2731 0.1557 0.042 Uiso 1 1 calc R . .
H24B H 0.7127 0.2746 0.1877 0.042 Uiso 1 1 calc R . .
H24C H 0.6990 0.3100 0.1215 0.042 Uiso 1 1 calc R . .
C25 C 0.7597(2) 0.45692(14) 0.17896(10) 0.0390(5) Uani 1 1 d . . .
H25A H 0.7905 0.4596 0.1381 0.058 Uiso 1 1 calc R . .
H25B H 0.8280 0.4263 0.2030 0.058 Uiso 1 1 calc R . .
H25C H 0.7454 0.5190 0.1937 0.058 Uiso 1 1 calc R . .
C26 C 0.24136(18) 0.63784(11) 0.16995(7) 0.0186(3) Uani 1 1 d . . .
H26 H 0.2304 0.6207 0.2122 0.022 Uiso 1 1 calc R . .
C27 C 0.10094(19) 0.63790(12) 0.14161(8) 0.0242(4) Uani 1 1 d . . .
H27A H 0.1084 0.6575 0.1006 0.036 Uiso 1 1 calc R . .
H27B H 0.0419 0.6800 0.1630 0.036 Uiso 1 1 calc R . .
H27C H 0.0629 0.5762 0.1432 0.036 Uiso 1 1 calc R . .
C28 C 0.3019(2) 0.73430(12) 0.16758(8) 0.0281(4) Uani 1 1 d . . .
H28A H 0.3889 0.7348 0.1880 0.042 Uiso 1 1 calc R . .
H28B H 0.2403 0.7774 0.1866 0.042 Uiso 1 1 calc R . .
H28C H 0.3152 0.7523 0.1266 0.042 Uiso 1 1 calc R . .
C29 C 0.5890(2) 0.54822(14) 0.50184(8) 0.0303(4) Uani 1 1 d . . .
C30 C 0.6381(2) 0.62290(14) 0.46992(8) 0.0354(5) Uani 1 1 d . . .
H30 H 0.7245 0.6196 0.4520 0.043 Uiso 1 1 calc R . .
C31 C 0.5618(3) 0.70113(15) 0.46433(9) 0.0391(5) Uani 1 1 d . . .
H31 H 0.5959 0.7509 0.4421 0.047 Uiso 1 1 calc R . .
C32 C 0.4371(3) 0.70823(15) 0.49048(9) 0.0425(6) Uani 1 1 d . . .
H32 H 0.3856 0.7626 0.4865 0.051 Uiso 1 1 calc R . .
C33 C 0.3876(3) 0.63599(16) 0.52248(9) 0.0429(5) Uani 1 1 d . . .
H33 H 0.3018 0.6403 0.5408 0.051 Uiso 1 1 calc R . .
C34 C 0.4635(2) 0.55661(14) 0.52798(8) 0.0342(5) Uani 1 1 d . . .
H34 H 0.4286 0.5071 0.5502 0.041 Uiso 1 1 calc R . .
C35 C 0.6675(2) 0.46089(15) 0.50604(10) 0.0456(5) Uani 1 1 d . . .
H35A H 0.6289 0.4224 0.5369 0.068 Uiso 1 1 calc R . .
H35B H 0.7618 0.4747 0.5155 0.068 Uiso 1 1 calc R . .
H35C H 0.6632 0.4286 0.4684 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ge1 C1 2.1894(16) . ?
Ge1 Cl2 2.2773(4) . ?
Ge1 Cl1 2.2807(5) . ?
N1 C1 1.3396(17) . ?
N1 C5 1.453(2) . ?
N1 C2 1.486(2) . ?
C1 N2 1.341(2) . ?
N2 C17 1.4537(18) . ?
N2 C4 1.483(2) . ?
C2 C3 1.511(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.507(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.395(2) . ?
C5 C6 1.405(2) . ?
C6 C7 1.394(2) . ?
C6 C11 1.525(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C14 1.530(2) . ?
C11 C12 1.528(2) . ?
C11 C13 1.536(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.529(2) . ?
C14 C16 1.533(2) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.406(2) . ?
C17 C18 1.407(2) . ?
C18 C19 1.393(2) . ?
C18 C23 1.521(2) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(2) . ?
C21 H21 0.9500 . ?
C22 C26 1.523(2) . ?
C23 C24 1.531(2) . ?
C23 C25 1.548(3) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.534(2) . ?
C26 C28 1.536(2) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.384(3) . ?
C29 C30 1.401(3) . ?
C29 C35 1.501(3) . ?
C30 C31 1.379(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.376(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ge1 Cl2 103.42(4) . . ?
C1 Ge1 Cl1 91.62(4) . . ?
Cl2 Ge1 Cl1 94.595(17) . . ?
C1 N1 C5 122.40(14) . . ?
C1 N1 C2 124.22(14) . . ?
C5 N1 C2 113.10(12) . . ?
N1 C1 N2 118.36(15) . . ?
N1 C1 Ge1 130.44(13) . . ?
N2 C1 Ge1 111.06(10) . . ?
C1 N2 C17 121.29(13) . . ?
C1 N2 C4 122.62(13) . . ?
C17 N2 C4 115.76(13) . . ?
N1 C2 C3 110.92(13) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 108.19(15) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 109.67(13) . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 122.39(15) . . ?
C10 C5 N1 118.67(13) . . ?
C6 C5 N1 118.85(15) . . ?
C7 C6 C5 117.41(15) . . ?
C7 C6 C11 119.14(14) . . ?
C5 C6 C11 123.44(15) . . ?
C8 C7 C6 121.17(15) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.07(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.10(16) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C9 117.72(14) . . ?
C5 C10 C14 123.51(14) . . ?
C9 C10 C14 118.76(15) . . ?
C6 C11 C12 111.23(15) . . ?
C6 C11 C13 110.52(14) . . ?
C12 C11 C13 110.45(15) . . ?
C6 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C13 C11 H11 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C10 110.72(14) . . ?
C15 C14 C16 111.14(15) . . ?
C10 C14 C16 111.31(13) . . ?
C15 C14 H14 107.8 . . ?
C10 C14 H14 107.8 . . ?
C16 C14 H14 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 122.45(14) . . ?
C22 C17 N2 118.66(14) . . ?
C18 C17 N2 118.80(14) . . ?
C19 C18 C17 117.31(15) . . ?
C19 C18 C23 119.04(15) . . ?
C17 C18 C23 123.43(14) . . ?
C20 C19 C18 121.27(16) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 120.04(15) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.33(15) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C17 117.36(15) . . ?
C21 C22 C26 119.48(15) . . ?
C17 C22 C26 123.12(14) . . ?
C18 C23 C24 114.34(14) . . ?
C18 C23 C25 109.21(14) . . ?
C24 C23 C25 107.25(15) . . ?
C18 C23 H23 108.6 . . ?
C24 C23 H23 108.6 . . ?
C25 C23 H23 108.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C27 112.61(14) . . ?
C22 C26 C28 110.67(14) . . ?
C27 C26 C28 109.83(15) . . ?
C22 C26 H26 107.9 . . ?
C27 C26 H26 107.9 . . ?
C28 C26 H26 107.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 117.80(19) . . ?
C34 C29 C35 120.95(19) . . ?
C30 C29 C35 121.2(2) . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 121.0(2) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C33 C32 C31 119.4(2) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 119.9(2) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 121.43(19) . . ?
C29 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 1012342'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 Cl3 N2 P'
_chemical_formula_weight         541.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.1527(16)
_cell_length_b                   10.830(2)
_cell_length_c                   31.317(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.02(3)
_cell_angle_gamma                90.00
_cell_volume                     2754.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   'SCALE3 ABSPACK'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24625
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6635
_reflns_number_gt                5910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 The Level A alert relating to the short P(1)..Cl(3) intermolecular contact
 is spurios, as this is in reality a long intramolecular bond. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+1.5423P] where P=(Fo²+2Fc²)/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         6635
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Cl1 Cl 0.50548(5) 0.46634(3) 0.160368(14) 0.02609(10) Uani 1 1 d . . .
P1 P 0.59037(5) 0.32525(3) 0.115786(12) 0.01576(9) Uani 1 1 d . . .
N1 N 0.37990(14) 0.12825(10) 0.14556(4) 0.0127(2) Uani 1 1 d . . .
C1 C 0.39746(17) 0.22503(12) 0.11964(4) 0.0125(3) Uani 1 1 d . . .
Cl2 Cl 0.76293(4) 0.26552(3) 0.163479(12) 0.01921(9) Uani 1 1 d . . .
N2 N 0.27483(14) 0.25561(11) 0.09058(4) 0.0139(2) Uani 1 1 d . . .
C2 C 0.25089(18) 0.03203(13) 0.13651(5) 0.0166(3) Uani 1 1 d . . .
H2A H 0.1736 0.0343 0.1592 0.020 Uiso 1 1 calc R . .
H2B H 0.3035 -0.0504 0.1372 0.020 Uiso 1 1 calc R . .
Cl3 Cl 0.67873(5) 0.15495(3) 0.072190(12) 0.02122(9) Uani 1 1 d . . .
C3 C 0.15608(18) 0.05085(14) 0.09346(5) 0.0180(3) Uani 1 1 d . . .
H3A H 0.0531 0.0020 0.0915 0.022 Uiso 1 1 calc R . .
H3B H 0.2229 0.0245 0.0702 0.022 Uiso 1 1 calc R . .
C4 C 0.11750(18) 0.18735(14) 0.08973(5) 0.0198(3) Uani 1 1 d . . .
H4A H 0.0496 0.2042 0.0626 0.024 Uiso 1 1 calc R . .
H4B H 0.0552 0.2140 0.1139 0.024 Uiso 1 1 calc R . .
C5 C 0.46995(17) 0.11107(12) 0.18743(4) 0.0129(3) Uani 1 1 d . . .
C6 C 0.42184(17) 0.18036(13) 0.22217(5) 0.0149(3) Uani 1 1 d . . .
C7 C 0.50768(19) 0.16047(14) 0.26208(5) 0.0185(3) Uani 1 1 d . . .
H7 H 0.4818 0.2092 0.2858 0.022 Uiso 1 1 calc R . .
C8 C 0.62953(19) 0.07166(14) 0.26806(5) 0.0193(3) Uani 1 1 d . . .
H8 H 0.6870 0.0604 0.2955 0.023 Uiso 1 1 calc R . .
C9 C 0.66707(18) -0.00065(13) 0.23383(5) 0.0171(3) Uani 1 1 d . . .
H9 H 0.7476 -0.0638 0.2384 0.021 Uiso 1 1 calc R . .
C10 C 0.58951(17) 0.01692(12) 0.19279(5) 0.0141(3) Uani 1 1 d . . .
C11 C 0.27527(19) 0.26888(13) 0.21904(5) 0.0180(3) Uani 1 1 d . . .
H11 H 0.2538 0.2962 0.1886 0.022 Uiso 1 1 calc R . .
C12 C 0.3056(2) 0.38391(15) 0.24738(6) 0.0280(4) Uani 1 1 d . . .
H12A H 0.3068 0.3602 0.2776 0.042 Uiso 1 1 calc R . .
H12B H 0.2175 0.4441 0.2405 0.042 Uiso 1 1 calc R . .
H12C H 0.4118 0.4208 0.2422 0.042 Uiso 1 1 calc R . .
C13 C 0.1205(2) 0.20388(15) 0.23243(6) 0.0241(3) Uani 1 1 d . . .
H13A H 0.0921 0.1349 0.2129 0.036 Uiso 1 1 calc R . .
H13B H 0.0288 0.2627 0.2312 0.036 Uiso 1 1 calc R . .
H13C H 0.1416 0.1725 0.2617 0.036 Uiso 1 1 calc R . .
C14 C 0.63648(18) -0.06583(13) 0.15661(5) 0.0164(3) Uani 1 1 d . . .
H14 H 0.5778 -0.0360 0.1292 0.020 Uiso 1 1 calc R . .
C15 C 0.82164(19) -0.06360(15) 0.15206(5) 0.0228(3) Uani 1 1 d . . .
H15A H 0.8559 0.0208 0.1459 0.034 Uiso 1 1 calc R . .
H15B H 0.8467 -0.1181 0.1285 0.034 Uiso 1 1 calc R . .
H15C H 0.8810 -0.0921 0.1788 0.034 Uiso 1 1 calc R . .
C16 C 0.5826(2) -0.19924(14) 0.16431(5) 0.0228(3) Uani 1 1 d . . .
H16A H 0.6416 -0.2306 0.1907 0.034 Uiso 1 1 calc R . .
H16B H 0.6081 -0.2510 0.1401 0.034 Uiso 1 1 calc R . .
H16C H 0.4638 -0.2013 0.1671 0.034 Uiso 1 1 calc R . .
C17 C 0.28166(17) 0.35317(13) 0.05843(5) 0.0150(3) Uani 1 1 d . . .
C18 C 0.22451(18) 0.47171(13) 0.06833(5) 0.0167(3) Uani 1 1 d . . .
C19 C 0.2278(2) 0.56248(14) 0.03671(5) 0.0215(3) Uani 1 1 d . . .
H19 H 0.1934 0.6440 0.0427 0.026 Uiso 1 1 calc R . .
C20 C 0.2801(2) 0.53648(15) -0.00313(5) 0.0238(3) Uani 1 1 d . . .
H20 H 0.2863 0.6004 -0.0237 0.029 Uiso 1 1 calc R . .
C21 C 0.3235(2) 0.41698(15) -0.01292(5) 0.0215(3) Uani 1 1 d . . .
H21 H 0.3555 0.3995 -0.0407 0.026 Uiso 1 1 calc R . .
C22 C 0.32142(18) 0.32146(13) 0.01680(5) 0.0168(3) Uani 1 1 d . . .
C23 C 0.14590(19) 0.50315(14) 0.10918(5) 0.0199(3) Uani 1 1 d . . .
H23 H 0.1852 0.4426 0.1319 0.024 Uiso 1 1 calc R . .
C24 C 0.1876(2) 0.63469(16) 0.12567(6) 0.0295(4) Uani 1 1 d . . .
H24A H 0.3054 0.6504 0.1243 0.044 Uiso 1 1 calc R . .
H24B H 0.1601 0.6423 0.1554 0.044 Uiso 1 1 calc R . .
H24C H 0.1238 0.6950 0.1078 0.044 Uiso 1 1 calc R . .
C25 C -0.0412(2) 0.49261(17) 0.10128(6) 0.0280(4) Uani 1 1 d . . .
H25A H -0.0820 0.5547 0.0802 0.042 Uiso 1 1 calc R . .
H25B H -0.0912 0.5063 0.1282 0.042 Uiso 1 1 calc R . .
H25C H -0.0704 0.4100 0.0903 0.042 Uiso 1 1 calc R . .
C26 C 0.34178(19) 0.18901(14) 0.00181(5) 0.0192(3) Uani 1 1 d . . .
H26 H 0.3687 0.1361 0.0277 0.023 Uiso 1 1 calc R . .
C27 C 0.4782(2) 0.17215(15) -0.02845(5) 0.0253(3) Uani 1 1 d . . .
H27A H 0.4520 0.2209 -0.0545 0.038 Uiso 1 1 calc R . .
H27B H 0.4865 0.0847 -0.0360 0.038 Uiso 1 1 calc R . .
H27C H 0.5834 0.2001 -0.0141 0.038 Uiso 1 1 calc R . .
C28 C 0.1777(2) 0.14360(17) -0.02094(6) 0.0302(4) Uani 1 1 d . . .
H28A H 0.0906 0.1507 -0.0014 0.045 Uiso 1 1 calc R . .
H28B H 0.1888 0.0571 -0.0294 0.045 Uiso 1 1 calc R . .
H28C H 0.1492 0.1941 -0.0465 0.045 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 P1 2.2209(7) . ?
P1 C1 1.9234(14) . ?
P1 Cl2 2.0642(8) . ?
P1 Cl3 2.4406(7) . ?
N1 C1 1.3409(17) . ?
N1 C5 1.4577(18) . ?
N1 C2 1.4901(17) . ?
C1 N2 1.3336(18) . ?
N2 C17 1.4639(17) . ?
N2 C4 1.4787(18) . ?
C2 C3 1.508(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.405(2) . ?
C5 C10 1.4104(19) . ?
C6 C7 1.395(2) . ?
C6 C11 1.528(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C14 1.520(2) . ?
C11 C13 1.535(2) . ?
C11 C12 1.537(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.529(2) . ?
C14 C16 1.535(2) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.409(2) . ?
C17 C22 1.413(2) . ?
C18 C19 1.397(2) . ?
C18 C23 1.519(2) . ?
C19 C20 1.382(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(2) . ?
C21 H21 0.9500 . ?
C22 C26 1.523(2) . ?
C23 C25 1.528(2) . ?
C23 C24 1.543(2) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.534(2) . ?
C26 C28 1.540(2) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 Cl2 106.68(5) . . ?
C1 P1 Cl1 92.71(5) . . ?
Cl2 P1 Cl1 89.48(2) . . ?
C1 P1 Cl3 83.78(5) . . ?
Cl2 P1 Cl3 87.26(2) . . ?
Cl1 P1 Cl3 174.31(2) . . ?
C1 N1 C5 124.91(11) . . ?
C1 N1 C2 122.85(12) . . ?
C5 N1 C2 111.92(11) . . ?
N2 C1 N1 119.60(12) . . ?
N2 C1 P1 112.66(10) . . ?
N1 C1 P1 127.61(10) . . ?
C1 N2 C17 125.27(12) . . ?
C1 N2 C4 119.04(12) . . ?
C17 N2 C4 115.69(11) . . ?
N1 C2 C3 111.93(11) . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C4 106.73(12) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
N2 C4 C3 108.23(12) . . ?
N2 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
N2 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 C10 122.06(13) . . ?
C6 C5 N1 118.39(12) . . ?
C10 C5 N1 119.19(12) . . ?
C7 C6 C5 117.33(13) . . ?
C7 C6 C11 118.85(13) . . ?
C5 C6 C11 123.70(13) . . ?
C8 C7 C6 121.78(14) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 119.57(14) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 121.58(14) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C5 117.46(13) . . ?
C9 C10 C14 118.89(13) . . ?
C5 C10 C14 123.66(13) . . ?
C6 C11 C13 110.59(12) . . ?
C6 C11 C12 112.71(13) . . ?
C13 C11 C12 107.96(13) . . ?
C6 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 C15 112.04(12) . . ?
C10 C14 C16 110.10(12) . . ?
C15 C14 C16 109.13(12) . . ?
C10 C14 H14 108.5 . . ?
C15 C14 H14 108.5 . . ?
C16 C14 H14 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 122.09(13) . . ?
C18 C17 N2 118.22(13) . . ?
C22 C17 N2 119.00(12) . . ?
C19 C18 C17 117.24(14) . . ?
C19 C18 C23 118.36(13) . . ?
C17 C18 C23 124.15(13) . . ?
C20 C19 C18 121.53(14) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C19 C20 C21 119.71(14) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C22 121.92(15) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C21 C22 C17 116.95(14) . . ?
C21 C22 C26 119.05(13) . . ?
C17 C22 C26 123.60(13) . . ?
C18 C23 C25 109.61(13) . . ?
C18 C23 C24 113.07(13) . . ?
C25 C23 C24 108.11(14) . . ?
C18 C23 H23 108.7 . . ?
C25 C23 H23 108.7 . . ?
C24 C23 H23 108.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C27 114.02(13) . . ?
C22 C26 C28 109.25(13) . . ?
C27 C26 C28 108.88(13) . . ?
C22 C26 H26 108.2 . . ?
C27 C26 H26 108.2 . . ?
C28 C26 H26 108.2 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 1012343'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 Cl3 N2 Sb'
_chemical_formula_weight         632.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.7102(5)
_cell_length_b                   15.3670(5)
_cell_length_c                   11.5589(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.300(7)
_cell_angle_gamma                90.00
_cell_volume                     1460.21(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    1.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_process_details   'SCALE3 ABSPACK'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11963
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.99
_reflns_number_total             6677
_reflns_number_gt                6378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0197P)²+0.2304P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(11)
_refine_ls_number_reflns         6677
_refine_ls_number_parameters     315
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0501
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_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
Sb1 Sb 0.792688(16) 0.010721(11) 0.720797(12) 0.01660(4) Uani 1 1 d . . .
Cl1 Cl 0.70236(8) 0.13366(4) 0.82836(6) 0.02604(14) Uani 1 1 d . . .
N1 N 0.9239(2) 0.13739(12) 0.54421(18) 0.0147(4) Uani 1 1 d . . .
C1 C 0.9592(3) 0.09578(15) 0.6511(2) 0.0138(4) Uani 1 1 d . . .
Cl2 Cl 0.53889(6) 0.02327(5) 0.56192(5) 0.02264(15) Uani 1 1 d . . .
N2 N 1.1133(2) 0.08569(13) 0.72238(18) 0.0154(4) Uani 1 1 d . . .
C2 C 1.0537(3) 0.17193(17) 0.4985(2) 0.0210(5) Uani 1 1 d . . .
H2A H 1.0154 0.2265 0.4524 0.025 Uiso 1 1 calc R . .
H2B H 1.0752 0.1292 0.4415 0.025 Uiso 1 1 calc R . .
Cl3 Cl 0.86234(8) -0.10134(4) 0.57997(7) 0.02836(14) Uani 1 1 d . . .
C3 C 1.2088(3) 0.18946(19) 0.6021(3) 0.0295(6) Uani 1 1 d . . .
H3A H 1.2974 0.2033 0.5691 0.035 Uiso 1 1 calc R . .
H3B H 1.1940 0.2399 0.6506 0.035 Uiso 1 1 calc R . .
C4 C 1.2521(3) 0.11056(17) 0.6817(2) 0.0217(5) Uani 1 1 d . . .
H4A H 1.2788 0.0619 0.6355 0.026 Uiso 1 1 calc R . .
H4B H 1.3490 0.1228 0.7540 0.026 Uiso 1 1 calc R . .
C5 C 0.7588(3) 0.15793(15) 0.4660(2) 0.0157(5) Uani 1 1 d . . .
C6 C 0.6777(3) 0.22748(15) 0.4996(2) 0.0175(5) Uani 1 1 d . . .
C7 C 0.5222(3) 0.24841(17) 0.4202(2) 0.0205(5) Uani 1 1 d . . .
H7 H 0.4629 0.2942 0.4410 0.025 Uiso 1 1 calc R . .
C8 C 0.4539(3) 0.20329(18) 0.3120(2) 0.0252(6) Uani 1 1 d . . .
H8 H 0.3479 0.2180 0.2595 0.030 Uiso 1 1 calc R . .
C9 C 0.5382(3) 0.13715(18) 0.2795(2) 0.0231(5) Uani 1 1 d . . .
H9 H 0.4899 0.1075 0.2040 0.028 Uiso 1 1 calc R . .
C10 C 0.6930(3) 0.11274(15) 0.3551(2) 0.0176(5) Uani 1 1 d . . .
C11 C 0.7530(3) 0.28226(16) 0.6138(2) 0.0203(5) Uani 1 1 d . . .
H11 H 0.8269 0.2439 0.6782 0.024 Uiso 1 1 calc R . .
C12 C 0.6277(4) 0.32179(18) 0.6661(2) 0.0272(6) Uani 1 1 d . . .
H12A H 0.5710 0.3699 0.6136 0.041 Uiso 1 1 calc R . .
H12B H 0.6835 0.3436 0.7491 0.041 Uiso 1 1 calc R . .
H12C H 0.5487 0.2771 0.6689 0.041 Uiso 1 1 calc R . .
C13 C 0.8562(4) 0.35647(19) 0.5883(3) 0.0358(7) Uani 1 1 d . . .
H13A H 0.9458 0.3318 0.5653 0.054 Uiso 1 1 calc R . .
H13B H 0.9004 0.3921 0.6622 0.054 Uiso 1 1 calc R . .
H13C H 0.7880 0.3927 0.5212 0.054 Uiso 1 1 calc R . .
C14 C 0.7834(3) 0.04074(16) 0.3135(2) 0.0204(5) Uani 1 1 d . . .
H14 H 0.8812 0.0247 0.3846 0.024 Uiso 1 1 calc R . .
C15 C 0.6792(4) -0.04110(19) 0.2727(2) 0.0297(6) Uani 1 1 d . . .
H15A H 0.6332 -0.0579 0.3362 0.045 Uiso 1 1 calc R . .
H15B H 0.7468 -0.0886 0.2598 0.045 Uiso 1 1 calc R . .
H15C H 0.5908 -0.0292 0.1960 0.045 Uiso 1 1 calc R . .
C16 C 0.8426(4) 0.07307(19) 0.2093(3) 0.0319(6) Uani 1 1 d . . .
H16A H 0.7486 0.0874 0.1374 0.048 Uiso 1 1 calc R . .
H16B H 0.9069 0.0273 0.1879 0.048 Uiso 1 1 calc R . .
H16C H 0.9101 0.1251 0.2365 0.048 Uiso 1 1 calc R . .
C17 C 1.1492(3) 0.05691(17) 0.8493(2) 0.0154(5) Uani 1 1 d . . .
C18 C 1.1337(3) 0.11885(16) 0.9351(2) 0.0185(5) Uani 1 1 d . . .
C19 C 1.1515(3) 0.08826(17) 1.0515(2) 0.0226(5) Uani 1 1 d . . .
H19 H 1.1345 0.1271 1.1101 0.027 Uiso 1 1 calc R . .
C20 C 1.1931(3) 0.0031(2) 1.0846(2) 0.0240(5) Uani 1 1 d . . .
H20 H 1.2002 -0.0165 1.1642 0.029 Uiso 1 1 calc R . .
C21 C 1.2248(3) -0.05409(17) 1.0029(2) 0.0219(5) Uani 1 1 d . . .
H21 H 1.2610 -0.1114 1.0287 0.026 Uiso 1 1 calc R . .
C22 C 1.2038(3) -0.02795(17) 0.8813(2) 0.0173(5) Uani 1 1 d . . .
C23 C 1.1242(3) 0.21613(17) 0.9083(2) 0.0276(6) Uani 1 1 d . . .
H23 H 1.0657 0.2244 0.8187 0.033 Uiso 1 1 calc R . .
C24 C 1.0373(4) 0.2695(2) 0.9785(3) 0.0405(8) Uani 1 1 d . . .
H24A H 0.9276 0.2461 0.9632 0.061 Uiso 1 1 calc R . .
H24B H 1.0298 0.3302 0.9512 0.061 Uiso 1 1 calc R . .
H24C H 1.0984 0.2665 1.0664 0.061 Uiso 1 1 calc R . .
C25 C 1.2979(4) 0.25164(19) 0.9376(3) 0.0335(7) Uani 1 1 d . . .
H25A H 1.3588 0.2422 1.0246 0.050 Uiso 1 1 calc R . .
H25B H 1.2934 0.3141 0.9196 0.050 Uiso 1 1 calc R . .
H25C H 1.3523 0.2213 0.8874 0.050 Uiso 1 1 calc R . .
C26 C 1.2561(3) -0.08875(17) 0.7980(2) 0.0211(5) Uani 1 1 d . . .
H26 H 1.2037 -0.0687 0.7115 0.025 Uiso 1 1 calc R . .
C27 C 1.2089(4) -0.18409(17) 0.8060(3) 0.0295(6) Uani 1 1 d . . .
H27A H 1.2634 -0.2059 0.8892 0.044 Uiso 1 1 calc R . .
H27B H 1.2424 -0.2189 0.7474 0.044 Uiso 1 1 calc R . .
H27C H 1.0908 -0.1884 0.7865 0.044 Uiso 1 1 calc R . .
C28 C 1.4423(3) -0.08102(19) 0.8299(3) 0.0292(6) Uani 1 1 d . . .
H28A H 1.4713 -0.0201 0.8226 0.044 Uiso 1 1 calc R . .
H28B H 1.4776 -0.1169 0.7733 0.044 Uiso 1 1 calc R . .
H28C H 1.4961 -0.1011 0.9142 0.044 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 C1 2.288(2) . ?
Sb1 Cl2 2.3692(6) . ?
Sb1 Cl1 2.5260(7) . ?
Sb1 Cl3 2.5760(7) . ?
N1 C1 1.334(3) . ?
N1 C5 1.459(3) . ?
N1 C2 1.495(3) . ?
C1 N2 1.331(3) . ?
N2 C17 1.464(3) . ?
N2 C4 1.485(3) . ?
C2 C3 1.504(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.493(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.403(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.399(3) . ?
C6 C11 1.520(3) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C14 1.525(3) . ?
C11 C12 1.537(3) . ?
C11 C13 1.539(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.531(3) . ?
C14 C16 1.540(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.395(3) . ?
C17 C18 1.412(3) . ?
C18 C19 1.385(4) . ?
C18 C23 1.523(4) . ?
C19 C20 1.378(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.414(4) . ?
C21 H21 0.9500 . ?
C22 C26 1.516(3) . ?
C23 C24 1.520(4) . ?
C23 C25 1.537(4) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.533(4) . ?
C26 C28 1.544(4) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Sb1 Cl2 102.61(6) . . ?
C1 Sb1 Cl1 94.75(6) . . ?
Cl2 Sb1 Cl1 87.59(2) . . ?
C1 Sb1 Cl3 81.40(6) . . ?
Cl2 Sb1 Cl3 85.35(2) . . ?
Cl1 Sb1 Cl3 171.01(2) . . ?
C1 N1 C5 123.78(19) . . ?
C1 N1 C2 121.90(19) . . ?
C5 N1 C2 114.22(18) . . ?
N2 C1 N1 120.3(2) . . ?
N2 C1 Sb1 110.03(15) . . ?
N1 C1 Sb1 128.41(16) . . ?
C1 N2 C17 119.51(19) . . ?
C1 N2 C4 122.27(19) . . ?
C17 N2 C4 117.96(19) . . ?
N1 C2 C3 111.5(2) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 108.8(2) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C3 109.7(2) . . ?
N2 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C5 C6 122.6(2) . . ?
C10 C5 N1 118.7(2) . . ?
C6 C5 N1 118.5(2) . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 C11 119.2(2) . . ?
C5 C6 C11 123.3(2) . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 117.2(2) . . ?
C9 C10 C14 119.4(2) . . ?
C5 C10 C14 123.4(2) . . ?
C6 C11 C12 113.7(2) . . ?
C6 C11 C13 110.8(2) . . ?
C12 C11 C13 108.5(2) . . ?
C6 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
C13 C11 H11 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 C15 112.2(2) . . ?
C10 C14 C16 110.7(2) . . ?
C15 C14 C16 110.0(2) . . ?
C10 C14 H14 107.9 . . ?
C15 C14 H14 107.9 . . ?
C16 C14 H14 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 123.1(2) . . ?
C22 C17 N2 119.3(2) . . ?
C18 C17 N2 117.5(2) . . ?
C19 C18 C17 116.6(2) . . ?
C19 C18 C23 120.8(2) . . ?
C17 C18 C23 122.0(2) . . ?
C20 C19 C18 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 116.7(2) . . ?
C17 C22 C26 123.7(2) . . ?
C21 C22 C26 119.3(2) . . ?
C24 C23 C18 115.1(3) . . ?
C24 C23 C25 108.6(2) . . ?
C18 C23 C25 108.7(2) . . ?
C24 C23 H23 108.1 . . ?
C18 C23 H23 108.1 . . ?
C25 C23 H23 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 C27 114.1(2) . . ?
C22 C26 C28 108.2(2) . . ?
C27 C26 C28 109.9(2) . . ?
C22 C26 H26 108.2 . . ?
C27 C26 H26 108.2 . . ?
C28 C26 H26 108.2 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 1012344'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H86 Cl2 N4 P4'
_chemical_formula_weight         1082.13

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   18.416(4)
_cell_length_b                   17.227(3)
_cell_length_c                   19.145(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.03(3)
_cell_angle_gamma                90.00
_cell_volume                     6070(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            lime-green
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   XDS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71090
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Australian Synchrotron'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52324
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.00
_reflns_number_total             13132
_reflns_number_gt                8217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu-Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CifTAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 A molecule of benzene of crystallisation was located in the asymmetric unit
 and its atomic positions were found to be disordered over two sites. This
 disorder was successfully modelled and the carbon atoms of both sets
 were refined anisotropically. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0987P)²+2.0654P] where P=(Fo²+2Fc²)/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         13132
_refine_ls_number_parameters     720
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1899
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.012
_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
Cl1 Cl 0.73333(5) 0.19604(5) 0.43061(5) 0.0401(2) Uani 1 1 d . . .
P1 P 1.06292(5) 0.31094(5) 0.14583(5) 0.0375(2) Uani 1 1 d . . .
N1 N 1.20690(15) 0.27124(15) 0.14319(13) 0.0305(6) Uani 1 1 d . . .
C1 C 1.14134(19) 0.24446(18) 0.12530(16) 0.0324(7) Uani 1 1 d . . .
Cl2 Cl 0.75817(5) 0.53073(5) 0.50563(4) 0.03493(19) Uani 1 1 d . . .
P2 P 1.04402(6) 0.29569(6) 0.25823(5) 0.0413(2) Uani 1 1 d . . .
N2 N 1.13180(15) 0.18644(15) 0.08011(14) 0.0332(6) Uani 1 1 d . . .
C2 C 1.27258(19) 0.24337(19) 0.10886(19) 0.0356(7) Uani 1 1 d . . .
H2A H 1.3154 0.2485 0.1413 0.043 Uiso 1 1 calc R . .
H2B H 1.2812 0.2752 0.0669 0.043 Uiso 1 1 calc R . .
P3 P 0.97130(6) 0.24003(6) 0.17904(6) 0.0447(3) Uani 1 1 d . . .
N3 N 0.80542(15) 0.33247(15) 0.25456(13) 0.0282(6) Uani 1 1 d . . .
C3 C 1.2626(2) 0.15883(19) 0.08787(18) 0.0361(8) Uani 1 1 d . . .
H3A H 1.3045 0.1414 0.0609 0.043 Uiso 1 1 calc R . .
H3B H 1.2602 0.1260 0.1302 0.043 Uiso 1 1 calc R . .
P4 P 0.94633(5) 0.35726(5) 0.21781(5) 0.0361(2) Uani 1 1 d . . .
N4 N 0.88327(15) 0.36213(15) 0.34853(13) 0.0285(6) Uani 1 1 d . . .
C4 C 1.19402(19) 0.1506(2) 0.04430(19) 0.0383(8) Uani 1 1 d . . .
H4A H 1.1999 0.1760 -0.0015 0.046 Uiso 1 1 calc R . .
H4B H 1.1839 0.0948 0.0358 0.046 Uiso 1 1 calc R . .
C5 C 1.21568(18) 0.33093(18) 0.19646(16) 0.0306(7) Uani 1 1 d . . .
C6 C 1.2327(2) 0.3071(2) 0.26528(17) 0.0357(7) Uani 1 1 d . . .
C7 C 1.2374(2) 0.3641(2) 0.31648(18) 0.0431(9) Uani 1 1 d . . .
H7 H 1.2481 0.3498 0.3636 0.052 Uiso 1 1 calc R . .
C8 C 1.2266(2) 0.4414(2) 0.29974(19) 0.0448(9) Uani 1 1 d . . .
H8 H 1.2284 0.4794 0.3357 0.054 Uiso 1 1 calc R . .
C9 C 1.2134(2) 0.4639(2) 0.23142(19) 0.0433(9) Uani 1 1 d . . .
H9 H 1.2076 0.5174 0.2205 0.052 Uiso 1 1 calc R . .
C10 C 1.2083(2) 0.40859(19) 0.17795(17) 0.0357(8) Uani 1 1 d . . .
C11 C 1.2490(2) 0.2233(2) 0.28467(19) 0.0428(8) Uani 1 1 d . . .
H11 H 1.2369 0.1903 0.2429 0.051 Uiso 1 1 calc R . .
C12 C 1.2042(3) 0.1944(2) 0.3451(2) 0.0518(10) Uani 1 1 d . . .
H12A H 1.2119 0.2288 0.3854 0.078 Uiso 1 1 calc R . .
H12B H 1.2193 0.1416 0.3577 0.078 Uiso 1 1 calc R . .
H12C H 1.1526 0.1944 0.3307 0.078 Uiso 1 1 calc R . .
C13 C 1.3304(3) 0.2140(3) 0.3025(3) 0.0713(14) Uani 1 1 d . . .
H13A H 1.3586 0.2359 0.2647 0.107 Uiso 1 1 calc R . .
H13B H 1.3421 0.1588 0.3081 0.107 Uiso 1 1 calc R . .
H13C H 1.3427 0.2415 0.3462 0.107 Uiso 1 1 calc R . .
C14 C 1.1973(2) 0.4351(2) 0.10207(18) 0.0401(8) Uani 1 1 d . . .
H14 H 1.1811 0.3892 0.0735 0.048 Uiso 1 1 calc R . .
C15 C 1.1388(3) 0.4982(2) 0.0940(2) 0.0528(10) Uani 1 1 d . . .
H15A H 1.0948 0.4813 0.1171 0.079 Uiso 1 1 calc R . .
H15B H 1.1275 0.5071 0.0443 0.079 Uiso 1 1 calc R . .
H15C H 1.1568 0.5464 0.1156 0.079 Uiso 1 1 calc R . .
C16 C 1.2695(2) 0.4630(2) 0.0749(2) 0.0512(10) Uani 1 1 d . . .
H16A H 1.2836 0.5115 0.0985 0.077 Uiso 1 1 calc R . .
H16B H 1.2645 0.4719 0.0245 0.077 Uiso 1 1 calc R . .
H16C H 1.3069 0.4235 0.0845 0.077 Uiso 1 1 calc R . .
C17 C 1.0607(2) 0.1552(2) 0.06282(18) 0.0386(8) Uani 1 1 d . . .
C18 C 1.0400(2) 0.0872(2) 0.0986(2) 0.0458(9) Uani 1 1 d . . .
C19 C 0.9710(2) 0.0590(3) 0.0829(2) 0.0519(11) Uani 1 1 d . . .
H19 H 0.9551 0.0130 0.1051 0.062 Uiso 1 1 calc R . .
C20 C 0.9251(2) 0.0963(3) 0.0356(2) 0.0573(12) Uani 1 1 d . . .
H20 H 0.8772 0.0770 0.0273 0.069 Uiso 1 1 calc R . .
C21 C 0.9473(2) 0.1612(3) 0.0001(2) 0.0557(11) Uani 1 1 d . . .
H21 H 0.9147 0.1853 -0.0329 0.067 Uiso 1 1 calc R . .
C22 C 1.0175(2) 0.1926(2) 0.01164(19) 0.0446(9) Uani 1 1 d . . .
C23 C 1.0899(2) 0.0460(2) 0.1512(2) 0.0477(10) Uani 1 1 d . . .
H23 H 1.1409 0.0569 0.1378 0.057 Uiso 1 1 calc R . .
C24 C 1.0820(4) 0.0765(3) 0.2240(3) 0.0839(18) Uani 1 1 d . . .
H24A H 1.0954 0.1316 0.2255 0.126 Uiso 1 1 calc R . .
H24B H 1.1141 0.0474 0.2565 0.126 Uiso 1 1 calc R . .
H24C H 1.0315 0.0706 0.2376 0.126 Uiso 1 1 calc R . .
C25 C 1.0812(4) -0.0414(3) 0.1529(3) 0.0851(18) Uani 1 1 d . . .
H25A H 1.0296 -0.0545 0.1553 0.128 Uiso 1 1 calc R . .
H25B H 1.1077 -0.0623 0.1940 0.128 Uiso 1 1 calc R . .
H25C H 1.1007 -0.0639 0.1104 0.128 Uiso 1 1 calc R . .
C26 C 1.0431(2) 0.2604(2) -0.0327(2) 0.0471(9) Uani 1 1 d . . .
H26 H 1.0912 0.2781 -0.0128 0.056 Uiso 1 1 calc R . .
C27 C 0.9917(3) 0.3299(3) -0.0343(2) 0.0621(12) Uani 1 1 d . . .
H27A H 0.9445 0.3143 -0.0551 0.093 Uiso 1 1 calc R . .
H27B H 1.0123 0.3715 -0.0623 0.093 Uiso 1 1 calc R . .
H27C H 0.9852 0.3485 0.0135 0.093 Uiso 1 1 calc R . .
C28 C 1.0542(3) 0.2312(3) -0.1082(2) 0.0591(12) Uani 1 1 d . . .
H28A H 1.0895 0.1886 -0.1072 0.089 Uiso 1 1 calc R . .
H28B H 1.0723 0.2739 -0.1366 0.089 Uiso 1 1 calc R . .
H28C H 1.0077 0.2127 -0.1285 0.089 Uiso 1 1 calc R . .
C29 C 0.87161(18) 0.34292(17) 0.28189(16) 0.0286(7) Uani 1 1 d . . .
C30 C 0.74010(19) 0.3439(2) 0.29637(17) 0.0356(7) Uani 1 1 d . . .
H30A H 0.7265 0.2944 0.3187 0.043 Uiso 1 1 calc R . .
H30B H 0.6988 0.3612 0.2657 0.043 Uiso 1 1 calc R . .
C31 C 0.75664(19) 0.40455(19) 0.35182(17) 0.0361(8) Uani 1 1 d . . .
H31A H 0.7657 0.4553 0.3294 0.043 Uiso 1 1 calc R . .
H31B H 0.7145 0.4103 0.3822 0.043 Uiso 1 1 calc R . .
C32 C 0.82232(19) 0.38027(19) 0.39488(17) 0.0335(7) Uani 1 1 d . . .
H32A H 0.8369 0.4226 0.4274 0.040 Uiso 1 1 calc R . .
H32B H 0.8106 0.3339 0.4229 0.040 Uiso 1 1 calc R . .
C33 C 0.79458(19) 0.31383(18) 0.18077(16) 0.0319(7) Uani 1 1 d . . .
C34 C 0.7961(2) 0.3734(2) 0.13152(17) 0.0365(8) Uani 1 1 d . . .
C35 C 0.7892(2) 0.3522(2) 0.06122(19) 0.0479(9) Uani 1 1 d . . .
H35 H 0.7920 0.3909 0.0261 0.058 Uiso 1 1 calc R . .
C36 C 0.7783(3) 0.2761(2) 0.0422(2) 0.0533(10) Uani 1 1 d . . .
H36 H 0.7738 0.2632 -0.0060 0.064 Uiso 1 1 calc R . .
C37 C 0.7738(2) 0.2182(2) 0.09124(19) 0.0473(9) Uani 1 1 d . . .
H37 H 0.7651 0.1662 0.0766 0.057 Uiso 1 1 calc R . .
C38 C 0.78197(19) 0.23536(19) 0.16261(18) 0.0357(7) Uani 1 1 d . . .
C39 C 0.8009(2) 0.45924(19) 0.15117(18) 0.0379(8) Uani 1 1 d . . .
H39 H 0.8139 0.4626 0.2022 0.045 Uiso 1 1 calc R . .
C40 C 0.8580(2) 0.5039(2) 0.1120(2) 0.0512(10) Uani 1 1 d . . .
H40A H 0.9051 0.4778 0.1182 0.077 Uiso 1 1 calc R . .
H40B H 0.8617 0.5569 0.1305 0.077 Uiso 1 1 calc R . .
H40C H 0.8441 0.5057 0.0622 0.077 Uiso 1 1 calc R . .
C41 C 0.7262(2) 0.4977(2) 0.1388(2) 0.0469(9) Uani 1 1 d . . .
H41A H 0.7101 0.4908 0.0898 0.070 Uiso 1 1 calc R . .
H41B H 0.7298 0.5532 0.1494 0.070 Uiso 1 1 calc R . .
H41C H 0.6909 0.4735 0.1692 0.070 Uiso 1 1 calc R . .
C42 C 0.7759(2) 0.17127(19) 0.21642(19) 0.0378(8) Uani 1 1 d . . .
H42 H 0.7939 0.1917 0.2628 0.045 Uiso 1 1 calc R . .
C43 C 0.8224(2) 0.1010(2) 0.1977(2) 0.0474(9) Uani 1 1 d . . .
H43A H 0.8033 0.0779 0.1540 0.071 Uiso 1 1 calc R . .
H43B H 0.8209 0.0625 0.2353 0.071 Uiso 1 1 calc R . .
H43C H 0.8727 0.1177 0.1918 0.071 Uiso 1 1 calc R . .
C44 C 0.6965(2) 0.1467(2) 0.2225(2) 0.0537(10) Uani 1 1 d . . .
H44A H 0.6670 0.1921 0.2338 0.081 Uiso 1 1 calc R . .
H44B H 0.6929 0.1078 0.2596 0.081 Uiso 1 1 calc R . .
H44C H 0.6787 0.1244 0.1780 0.081 Uiso 1 1 calc R . .
C45 C 0.95529(18) 0.36068(19) 0.38079(15) 0.0305(7) Uani 1 1 d . . .
C46 C 0.9987(2) 0.42761(19) 0.37967(16) 0.0352(7) Uani 1 1 d . . .
C47 C 1.0687(2) 0.4219(2) 0.41017(18) 0.0402(8) Uani 1 1 d . . .
H47 H 1.1001 0.4656 0.4097 0.048 Uiso 1 1 calc R . .
C48 C 1.0930(2) 0.3535(2) 0.44107(18) 0.0424(8) Uani 1 1 d . . .
H48 H 1.1407 0.3509 0.4615 0.051 Uiso 1 1 calc R . .
C49 C 1.0486(2) 0.2894(2) 0.44242(17) 0.0397(8) Uani 1 1 d . . .
H49 H 1.0660 0.2431 0.4642 0.048 Uiso 1 1 calc R . .
C50 C 0.97819(19) 0.2910(2) 0.41225(16) 0.0338(7) Uani 1 1 d . . .
C51 C 0.9727(2) 0.5039(2) 0.34814(19) 0.0393(8) Uani 1 1 d . . .
H51 H 0.9261 0.4939 0.3212 0.047 Uiso 1 1 calc R . .
C52 C 1.0268(3) 0.5385(2) 0.2980(2) 0.0535(10) Uani 1 1 d . . .
H52A H 1.0723 0.5508 0.3237 0.080 Uiso 1 1 calc R . .
H52B H 1.0064 0.5861 0.2771 0.080 Uiso 1 1 calc R . .
H52C H 1.0363 0.5009 0.2610 0.080 Uiso 1 1 calc R . .
C53 C 0.9569(2) 0.5616(2) 0.4070(2) 0.0482(9) Uani 1 1 d . . .
H53A H 0.9157 0.5429 0.4333 0.072 Uiso 1 1 calc R . .
H53B H 0.9452 0.6126 0.3867 0.072 Uiso 1 1 calc R . .
H53C H 0.9999 0.5662 0.4384 0.072 Uiso 1 1 calc R . .
C54 C 0.9297(2) 0.2203(2) 0.41615(18) 0.0385(8) Uani 1 1 d . . .
H54 H 0.8818 0.2332 0.3929 0.046 Uiso 1 1 calc R . .
C55 C 0.9608(3) 0.1505(2) 0.3792(3) 0.0675(14) Uani 1 1 d . . .
H55A H 0.9699 0.1641 0.3306 0.101 Uiso 1 1 calc R . .
H55B H 0.9261 0.1074 0.3803 0.101 Uiso 1 1 calc R . .
H55C H 1.0066 0.1349 0.4029 0.101 Uiso 1 1 calc R . .
C56 C 0.9169(2) 0.2019(3) 0.4931(2) 0.0647(13) Uani 1 1 d . . .
H56A H 0.9628 0.1861 0.5163 0.097 Uiso 1 1 calc R . .
H56B H 0.8815 0.1597 0.4960 0.097 Uiso 1 1 calc R . .
H56C H 0.8983 0.2483 0.5161 0.097 Uiso 1 1 calc R . .
C57 C 1.0828(7) 0.1421(9) 0.6069(14) 0.077(6) Uani 0.46(3) 1 d PD A 1
H57 H 1.1261 0.1444 0.5815 0.093 Uiso 0.46(3) 1 calc PR A 1
C58 C 1.0418(9) 0.0735(6) 0.6077(12) 0.081(6) Uani 0.46(3) 1 d PD A 1
H58 H 1.0579 0.0288 0.5837 0.098 Uiso 0.46(3) 1 calc PR A 1
C59 C 0.9773(10) 0.0711(9) 0.6438(12) 0.102(8) Uani 0.46(3) 1 d PD A 1
H59 H 0.9492 0.0248 0.6436 0.122 Uiso 0.46(3) 1 calc PR A 1
C60 C 0.9537(12) 0.1361(11) 0.6800(12) 0.117(9) Uani 0.46(3) 1 d PD A 1
H60 H 0.9111 0.1335 0.7065 0.141 Uiso 0.46(3) 1 calc PR A 1
C61 C 0.9933(16) 0.2053(9) 0.6770(8) 0.104(7) Uani 0.46(3) 1 d PD A 1
H61 H 0.9751 0.2512 0.6976 0.125 Uiso 0.46(3) 1 calc PR A 1
C62 C 1.0596(12) 0.2069(7) 0.6438(13) 0.084(7) Uani 0.46(3) 1 d PD A 1
H62 H 1.0890 0.2522 0.6463 0.101 Uiso 0.46(3) 1 calc PR A 1
C60A C 0.9910(13) 0.1280(11) 0.6707(8) 0.112(8) Uani 0.54(3) 1 d PD A 2
H60A H 0.9547 0.1299 0.7047 0.134 Uiso 0.54(3) 1 calc PR A 2
C58A C 1.0440(9) 0.0649(7) 0.5716(11) 0.103(6) Uani 0.54(3) 1 d PD A 2
H58A H 1.0444 0.0232 0.5392 0.124 Uiso 0.54(3) 1 calc PR A 2
C57A C 1.0957(8) 0.1244(8) 0.5682(11) 0.084(5) Uani 0.54(3) 1 d PD A 2
H57A H 1.1314 0.1230 0.5336 0.101 Uiso 0.54(3) 1 calc PR A 2
C62A C 1.0944(11) 0.1857(10) 0.6159(9) 0.087(6) Uani 0.54(3) 1 d PD A 2
H62A H 1.1281 0.2272 0.6124 0.105 Uiso 0.54(3) 1 calc PR A 2
C59A C 0.9921(11) 0.0671(9) 0.6230(11) 0.095(7) Uani 0.54(3) 1 d PD A 2
H59A H 0.9572 0.0266 0.6253 0.114 Uiso 0.54(3) 1 calc PR A 2
C61A C 1.0438(14) 0.1863(10) 0.6685(7) 0.105(9) Uani 0.54(3) 1 d PD A 2
H61A H 1.0452 0.2263 0.7028 0.126 Uiso 0.54(3) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.895(3) . ?
P1 P3 2.1952(14) . ?
P1 P2 2.2077(13) . ?
N1 C1 1.326(4) . ?
N1 C5 1.453(4) . ?
N1 C2 1.477(4) . ?
C1 N2 1.330(4) . ?
P2 P4 2.2050(15) . ?
P2 P3 2.2063(16) . ?
N2 C17 1.443(4) . ?
N2 C4 1.490(4) . ?
C2 C3 1.520(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
P3 P4 2.2056(13) . ?
N3 C29 1.322(4) . ?
N3 C33 1.456(4) . ?
N3 C30 1.482(4) . ?
C3 C4 1.496(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
P4 C29 1.892(3) . ?
N4 C29 1.328(4) . ?
N4 C45 1.443(4) . ?
N4 C32 1.488(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.389(5) . ?
C5 C6 1.405(5) . ?
C6 C7 1.388(5) . ?
C6 C11 1.517(5) . ?
C7 C8 1.382(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(5) . ?
C9 H9 0.9500 . ?
C10 C14 1.529(5) . ?
C11 C12 1.528(5) . ?
C11 C13 1.534(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.523(6) . ?
C14 C15 1.533(5) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.398(6) . ?
C17 C18 1.416(5) . ?
C18 C19 1.384(6) . ?
C18 C23 1.516(6) . ?
C19 C20 1.375(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.411(6) . ?
C21 H21 0.9500 . ?
C22 C26 1.528(6) . ?
C23 C24 1.503(6) . ?
C23 C25 1.513(6) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.525(6) . ?
C26 C28 1.551(5) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 C31 1.513(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.499(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.395(5) . ?
C33 C38 1.413(4) . ?
C34 C35 1.396(5) . ?
C34 C39 1.528(5) . ?
C35 C36 1.374(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.375(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.401(5) . ?
C37 H37 0.9500 . ?
C38 C42 1.517(5) . ?
C39 C40 1.521(5) . ?
C39 C41 1.539(5) . ?
C39 H39 1.0000 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C44 1.532(5) . ?
C42 C43 1.532(5) . ?
C42 H42 1.0000 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C50 1.401(5) . ?
C45 C46 1.404(5) . ?
C46 C47 1.400(5) . ?
C46 C51 1.518(5) . ?
C47 C48 1.385(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.375(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.401(5) . ?
C49 H49 0.9500 . ?
C50 C54 1.514(5) . ?
C51 C52 1.529(5) . ?
C51 C53 1.538(5) . ?
C51 H51 1.0000 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 C55 1.517(5) . ?
C54 C56 1.532(5) . ?
C54 H54 1.0000 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 C62 1.396(6) . ?
C57 C58 1.402(6) . ?
C57 H57 0.9500 . ?
C58 C59 1.396(6) . ?
C58 H58 0.9500 . ?
C59 C60 1.395(6) . ?
C59 H59 0.9500 . ?
C60 C61 1.400(6) . ?
C60 H60 0.9500 . ?
C61 C62 1.398(6) . ?
C61 H61 0.9500 . ?
C62 H62 0.9500 . ?
C60A C59A 1.392(6) . ?
C60A C61A 1.400(6) . ?
C60A H60A 0.9500 . ?
C58A C59A 1.396(6) . ?
C58A C57A 1.401(6) . ?
C58A H58A 0.9500 . ?
C57A C62A 1.398(6) . ?
C57A H57A 0.9500 . ?
C62A C61A 1.396(6) . ?
C62A H62A 0.9500 . ?
C59A H59A 0.9500 . ?
C61A H61A 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
C1 P1 P3 108.85(11) . . ?
C1 P1 P2 106.13(11) . . ?
P3 P1 P2 60.14(5) . . ?
C1 N1 C5 120.3(3) . . ?
C1 N1 C2 121.6(3) . . ?
C5 N1 C2 118.0(3) . . ?
N1 C1 N2 121.9(3) . . ?
N1 C1 P1 115.4(2) . . ?
N2 C1 P1 120.3(3) . . ?
P4 P2 P3 60.00(5) . . ?
P4 P2 P1 75.84(5) . . ?
P3 P2 P1 59.65(5) . . ?
C1 N2 C17 121.8(3) . . ?
C1 N2 C4 121.7(3) . . ?
C17 N2 C4 116.5(3) . . ?
N1 C2 C3 109.6(3) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
P1 P3 P4 76.09(5) . . ?
P1 P3 P2 60.21(5) . . ?
P4 P3 P2 59.97(5) . . ?
C29 N3 C33 120.5(3) . . ?
C29 N3 C30 121.5(3) . . ?
C33 N3 C30 117.9(3) . . ?
C4 C3 C2 109.3(3) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C29 P4 P2 108.22(11) . . ?
C29 P4 P3 105.29(10) . . ?
P2 P4 P3 60.03(5) . . ?
C29 N4 C45 121.4(3) . . ?
C29 N4 C32 121.7(3) . . ?
C45 N4 C32 116.7(2) . . ?
N2 C4 C3 110.6(3) . . ?
N2 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C10 C5 C6 122.5(3) . . ?
C10 C5 N1 119.7(3) . . ?
C6 C5 N1 117.8(3) . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 C11 119.6(3) . . ?
C5 C6 C11 122.9(3) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 117.7(3) . . ?
C5 C10 C14 122.5(3) . . ?
C9 C10 C14 119.7(3) . . ?
C6 C11 C12 112.8(3) . . ?
C6 C11 C13 109.7(3) . . ?
C12 C11 C13 110.3(3) . . ?
C6 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C13 C11 H11 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 C10 109.3(3) . . ?
C16 C14 C15 111.1(3) . . ?
C10 C14 C15 112.1(3) . . ?
C16 C14 H14 108.1 . . ?
C10 C14 H14 108.1 . . ?
C15 C14 H14 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 124.3(3) . . ?
C22 C17 N2 118.6(3) . . ?
C18 C17 N2 117.1(3) . . ?
C19 C18 C17 116.5(4) . . ?
C19 C18 C23 120.6(4) . . ?
C17 C18 C23 122.8(3) . . ?
C20 C19 C18 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 121.2(4) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 121.3(4) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 115.4(4) . . ?
C17 C22 C26 124.2(3) . . ?
C21 C22 C26 120.3(4) . . ?
C24 C23 C25 108.4(4) . . ?
C24 C23 C18 112.1(3) . . ?
C25 C23 C18 114.7(4) . . ?
C24 C23 H23 107.1 . . ?
C25 C23 H23 107.1 . . ?
C18 C23 H23 107.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C22 114.1(3) . . ?
C27 C26 C28 109.7(4) . . ?
C22 C26 C28 108.8(3) . . ?
C27 C26 H26 108.0 . . ?
C22 C26 H26 108.0 . . ?
C28 C26 H26 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 N4 122.0(3) . . ?
N3 C29 P4 116.3(2) . . ?
N4 C29 P4 119.6(2) . . ?
N3 C30 C31 108.9(3) . . ?
N3 C30 H30A 109.9 . . ?
C31 C30 H30A 109.9 . . ?
N3 C30 H30B 109.9 . . ?
C31 C30 H30B 109.9 . . ?
H30A C30 H30B 108.3 . . ?
C32 C31 C30 109.4(3) . . ?
C32 C31 H31A 109.8 . . ?
C30 C31 H31A 109.8 . . ?
C32 C31 H31B 109.8 . . ?
C30 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
N4 C32 C31 110.0(3) . . ?
N4 C32 H32A 109.7 . . ?
C31 C32 H32A 109.7 . . ?
N4 C32 H32B 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
C34 C33 C38 123.0(3) . . ?
C34 C33 N3 119.2(3) . . ?
C38 C33 N3 117.8(3) . . ?
C33 C34 C35 117.1(3) . . ?
C33 C34 C39 123.2(3) . . ?
C35 C34 C39 119.5(3) . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C37 121.6(4) . . ?
C35 C36 H36 119.2 . . ?
C37 C36 H36 119.2 . . ?
C36 C37 C38 120.4(3) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C37 C38 C33 116.9(3) . . ?
C37 C38 C42 120.0(3) . . ?
C33 C38 C42 123.0(3) . . ?
C40 C39 C34 113.8(3) . . ?
C40 C39 C41 109.7(3) . . ?
C34 C39 C41 109.5(3) . . ?
C40 C39 H39 107.9 . . ?
C34 C39 H39 107.9 . . ?
C41 C39 H39 107.9 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 C44 110.2(3) . . ?
C38 C42 C43 111.2(3) . . ?
C44 C42 C43 110.0(3) . . ?
C38 C42 H42 108.4 . . ?
C44 C42 H42 108.4 . . ?
C43 C42 H42 108.4 . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C50 C45 C46 123.2(3) . . ?
C50 C45 N4 117.2(3) . . ?
C46 C45 N4 119.6(3) . . ?
C47 C46 C45 116.9(3) . . ?
C47 C46 C51 120.0(3) . . ?
C45 C46 C51 123.1(3) . . ?
C48 C47 C46 121.1(4) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C49 C48 C47 120.5(4) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 121.2(4) . . ?
C48 C49 H49 119.4 . . ?
C50 C49 H49 119.4 . . ?
C45 C50 C49 117.0(3) . . ?
C45 C50 C54 122.8(3) . . ?
C49 C50 C54 120.1(3) . . ?
C46 C51 C52 112.6(3) . . ?
C46 C51 C53 109.5(3) . . ?
C52 C51 C53 110.6(3) . . ?
C46 C51 H51 108.0 . . ?
C52 C51 H51 108.0 . . ?
C53 C51 H51 108.0 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C50 C54 C55 112.5(3) . . ?
C50 C54 C56 108.9(3) . . ?
C55 C54 C56 111.0(4) . . ?
C50 C54 H54 108.1 . . ?
C55 C54 H54 108.1 . . ?
C56 C54 H54 108.1 . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C62 C57 C58 119.6(5) . . ?
C62 C57 H57 120.2 . . ?
C58 C57 H57 120.2 . . ?
C59 C58 C57 119.9(6) . . ?
C59 C58 H58 120.1 . . ?
C57 C58 H58 120.1 . . ?
C60 C59 C58 120.5(6) . . ?
C60 C59 H59 119.8 . . ?
C58 C59 H59 119.8 . . ?
C59 C60 C61 119.5(6) . . ?
C59 C60 H60 120.3 . . ?
C61 C60 H60 120.3 . . ?
C62 C61 C60 120.0(5) . . ?
C62 C61 H61 120.0 . . ?
C60 C61 H61 120.0 . . ?
C57 C62 C61 120.2(5) . . ?
C57 C62 H62 119.9 . . ?
C61 C62 H62 119.9 . . ?
C59A C60A C61A 119.7(6) . . ?
C59A C60A H60A 120.2 . . ?
C61A C60A H60A 120.2 . . ?
C59A C58A C57A 119.8(6) . . ?
C59A C58A H58A 120.1 . . ?
C57A C58A H58A 120.1 . . ?
C62A C57A C58A 119.7(5) . . ?
C62A C57A H57A 120.2 . . ?
C58A C57A H57A 120.2 . . ?
C61A C62A C57A 120.3(5) . . ?
C61A C62A H62A 119.9 . . ?
C57A C62A H62A 119.9 . . ?
C60A C59A C58A 120.6(6) . . ?
C60A C59A H59A 119.7 . . ?
C58A C59A H59A 119.7 . . ?
C62A C61A C60A 119.9(5) . . ?
C62A C61A H61A 120.1 . . ?
C60A C61A H61A 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 1012345'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cj1074

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H64 N4'
_chemical_formula_weight         721.05

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   C222(1)

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

_cell_length_a                   11.656(2)
_cell_length_b                   14.612(3)
_cell_length_c                   23.686(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4033.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   XDS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71090
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Australian Synchrotron'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15178
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3948
_reflns_number_gt                3743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu-Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CifTAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 During the course of refinement a half molecule of benzene was located in the 
 asymmetric unit and found to sit on a 2-fold rotation axis. The carbon atoms
 of this molecule were refined anisotropically. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0392P)²+1.9321P] where P=(Fo²+2Fc²)/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       0.0313(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     251
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.061
_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
N1 N 0.75338(10) 0.09662(8) 0.51138(5) 0.0182(3) Uani 1 1 d . . .
C1 C 0.86309(11) 0.05400(9) 0.49653(6) 0.0161(3) Uani 1 1 d . . .
H1 H 0.9248 0.0805 0.5209 0.019 Uiso 1 1 calc R . .
N2 N 0.88865(10) 0.07560(8) 0.43662(5) 0.0174(3) Uani 1 1 d . . .
C2 C 0.68691(12) 0.13119(10) 0.46326(6) 0.0205(3) Uani 1 1 d . . .
H2A H 0.6121 0.1549 0.4766 0.025 Uiso 1 1 calc R . .
H2B H 0.6721 0.0808 0.4363 0.025 Uiso 1 1 calc R . .
C3 C 0.75298(14) 0.20717(10) 0.43394(7) 0.0242(3) Uani 1 1 d . . .
H3A H 0.7633 0.2595 0.4600 0.029 Uiso 1 1 calc R . .
H3B H 0.7100 0.2287 0.4004 0.029 Uiso 1 1 calc R . .
C4 C 0.87043(13) 0.16947(10) 0.41589(6) 0.0222(3) Uani 1 1 d . . .
H4A H 0.8756 0.1699 0.3742 0.027 Uiso 1 1 calc R . .
H4B H 0.9317 0.2097 0.4308 0.027 Uiso 1 1 calc R . .
C5 C 0.73662(12) 0.14856(9) 0.56218(6) 0.0180(3) Uani 1 1 d . . .
C6 C 0.81628(12) 0.21069(10) 0.58544(6) 0.0200(3) Uani 1 1 d . . .
C7 C 0.78744(13) 0.25919(10) 0.63442(6) 0.0218(3) Uani 1 1 d . . .
H7 H 0.8428 0.2996 0.6501 0.026 Uiso 1 1 calc R . .
C8 C 0.68231(13) 0.25121(10) 0.66115(6) 0.0217(3) Uani 1 1 d . . .
C9 C 0.60429(12) 0.19034(10) 0.63740(6) 0.0210(3) Uani 1 1 d . . .
H9 H 0.5315 0.1830 0.6549 0.025 Uiso 1 1 calc R . .
C10 C 0.62827(13) 0.13974(10) 0.58914(6) 0.0196(3) Uani 1 1 d . . .
C11 C 0.93176(13) 0.23297(11) 0.56034(7) 0.0244(3) Uani 1 1 d . . .
H11A H 0.9888 0.1891 0.5741 0.037 Uiso 1 1 calc R . .
H11B H 0.9543 0.2950 0.5715 0.037 Uiso 1 1 calc R . .
H11C H 0.9272 0.2293 0.5191 0.037 Uiso 1 1 calc R . .
C12 C 0.65272(15) 0.30825(11) 0.71203(7) 0.0284(4) Uani 1 1 d . . .
H12A H 0.5997 0.3571 0.7009 0.043 Uiso 1 1 calc R . .
H12B H 0.7229 0.3352 0.7276 0.043 Uiso 1 1 calc R . .
H12C H 0.6163 0.2695 0.7407 0.043 Uiso 1 1 calc R . .
C13 C 0.53484(13) 0.07792(10) 0.56717(7) 0.0242(3) Uani 1 1 d . . .
H13A H 0.4778 0.1145 0.5468 0.036 Uiso 1 1 calc R . .
H13B H 0.4979 0.0465 0.5989 0.036 Uiso 1 1 calc R . .
H13C H 0.5682 0.0325 0.5415 0.036 Uiso 1 1 calc R . .
C14 C 0.98338(12) 0.03297(10) 0.40758(6) 0.0181(3) Uani 1 1 d . . .
C15 C 1.09916(13) 0.04530(10) 0.42366(6) 0.0198(3) Uani 1 1 d . . .
C16 C 1.18441(12) -0.00077(11) 0.39375(7) 0.0223(3) Uani 1 1 d . . .
H16 H 1.2619 0.0057 0.4056 0.027 Uiso 1 1 calc R . .
C17 C 1.16078(13) -0.05571(10) 0.34736(6) 0.0229(3) Uani 1 1 d . . .
C18 C 1.04730(13) -0.06039(10) 0.32958(6) 0.0224(3) Uani 1 1 d . . .
H18 H 1.0295 -0.0951 0.2968 0.027 Uiso 1 1 calc R . .
C19 C 0.95853(12) -0.01594(10) 0.35810(6) 0.0203(3) Uani 1 1 d . . .
C20 C 1.13457(12) 0.10909(11) 0.47028(6) 0.0224(3) Uani 1 1 d . . .
H20A H 1.1166 0.1722 0.4595 0.034 Uiso 1 1 calc R . .
H20B H 1.2173 0.1033 0.4769 0.034 Uiso 1 1 calc R . .
H20C H 1.0930 0.0933 0.5049 0.034 Uiso 1 1 calc R . .
C21 C 1.25535(15) -0.10545(12) 0.31649(7) 0.0302(4) Uani 1 1 d . . .
H21A H 1.3051 -0.1363 0.3439 0.045 Uiso 1 1 calc R . .
H21B H 1.3006 -0.0614 0.2946 0.045 Uiso 1 1 calc R . .
H21C H 1.2217 -0.1509 0.2909 0.045 Uiso 1 1 calc R . .
C22 C 0.83959(12) -0.01794(11) 0.33298(6) 0.0235(3) Uani 1 1 d . . .
H22A H 0.8240 -0.0790 0.3177 0.035 Uiso 1 1 calc R . .
H22B H 0.8344 0.0274 0.3026 0.035 Uiso 1 1 calc R . .
H22C H 0.7831 -0.0034 0.3623 0.035 Uiso 1 1 calc R . .
C23 C 1.4669(2) 0.02395(14) 0.22571(9) 0.0497(6) Uani 1 1 d D . .
H23 H 1.4436 -0.0322 0.2090 0.060 Uiso 1 1 calc R . .
C24 C 1.43510(17) 0.10580(18) 0.20194(9) 0.0519(6) Uani 1 1 d D . .
H24 H 1.3901 0.1067 0.1685 0.062 Uiso 1 1 calc R . .
C25 C 1.46831(19) 0.18558(16) 0.22645(12) 0.0634(8) Uani 1 1 d D . .
H25 H 1.4462 0.2421 0.2099 0.076 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.4359(18) . ?
N1 C1 1.4652(17) . ?
N1 C2 1.4680(18) . ?
C1 N2 1.4838(18) . ?
C1 C1 1.587(3) 3_556 ?
C1 H1 1.0000 . ?
N2 C14 1.4424(18) . ?
N2 C4 1.4722(18) . ?
C2 C3 1.519(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.536(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.411(2) . ?
C5 C10 1.421(2) . ?
C6 C7 1.400(2) . ?
C6 C11 1.507(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 C12 1.505(2) . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C13 1.508(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.403(2) . ?
C14 C15 1.414(2) . ?
C15 C16 1.394(2) . ?
C15 C20 1.503(2) . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 C21 1.509(2) . ?
C18 C19 1.396(2) . ?
C18 H18 0.9500 . ?
C19 C22 1.5090(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.373(3) . ?
C23 C23 1.386(5) 4_855 ?
C23 H23 0.9500 . ?
C24 C25 1.359(3) . ?
C24 H24 0.9500 . ?
C25 C25 1.338(6) 4_855 ?
C25 H25 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
C5 N1 C1 123.00(11) . . ?
C5 N1 C2 113.39(11) . . ?
C1 N1 C2 114.86(11) . . ?
N1 C1 N2 108.33(11) . . ?
N1 C1 C1 113.44(8) . 3_556 ?
N2 C1 C1 108.10(13) . 3_556 ?
N1 C1 H1 109.0 . . ?
N2 C1 H1 109.0 . . ?
C1 C1 H1 109.0 3_556 . ?
C14 N2 C4 110.71(11) . . ?
C14 N2 C1 121.20(11) . . ?
C4 N2 C1 119.22(11) . . ?
N1 C2 C3 109.81(12) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 C3 C4 108.47(12) . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 C3 111.70(12) . . ?
N2 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
N2 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C10 117.89(13) . . ?
C6 C5 N1 125.30(12) . . ?
C10 C5 N1 116.71(12) . . ?
C7 C6 C5 119.42(13) . . ?
C7 C6 C11 115.59(13) . . ?
C5 C6 C11 124.95(13) . . ?
C8 C7 C6 123.29(14) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C7 C8 C9 116.58(14) . . ?
C7 C8 C12 121.49(14) . . ?
C9 C8 C12 121.88(14) . . ?
C10 C9 C8 122.78(14) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C5 120.01(14) . . ?
C9 C10 C13 117.22(13) . . ?
C5 C10 C13 122.76(13) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.15(13) . . ?
C19 C14 N2 117.41(12) . . ?
C15 C14 N2 123.17(13) . . ?
C16 C15 C14 118.82(14) . . ?
C16 C15 C20 118.51(13) . . ?
C14 C15 C20 122.63(13) . . ?
C17 C16 C15 122.70(14) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 117.20(13) . . ?
C16 C17 C21 121.13(14) . . ?
C18 C17 C21 121.64(14) . . ?
C17 C18 C19 122.40(14) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C14 119.23(13) . . ?
C18 C19 C22 118.76(13) . . ?
C14 C19 C22 121.94(13) . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C23 119.40(13) . 4_855 ?
C24 C23 H23 120.3 . . ?
C23 C23 H23 120.3 4_855 . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C25 C25 C24 120.91(13) 4_855 . ?
C25 C25 H25 119.5 4_855 . ?
C24 C25 H25 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 1012346'
