# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ip298
_database_code_depnum_ccdc_archive 'CCDC 1050915'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H57 Ho N6'
_chemical_formula_weight         738.81

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'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.776(2)
_cell_length_b                   13.149(3)
_cell_length_c                   16.983(3)
_cell_angle_alpha                101.28(3)
_cell_angle_beta                 105.35(3)
_cell_angle_gamma                108.19(3)
_cell_volume                     1905.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    44289
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      29.65

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_correction_T_min  0.3176
_exptl_absorpt_correction_T_max  0.3338
_exptl_crystal_size_rad          0.4000
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21302
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         29.21
_reflns_number_total             10209
_reflns_number_gt                9422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0573P)²+0.5995P] 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       0.0092(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10209
_refine_ls_number_parameters     461
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.003
_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
Ho Ho 0.540510(12) 0.820133(9) 0.720479(7) 0.02638(6) Uani 1 1 d . A .
N1 N 0.7259(3) 0.9751(2) 0.70757(17) 0.0402(6) Uani 1 1 d . . .
N2 N 0.7211(3) 0.9729(2) 0.83899(15) 0.0360(5) Uani 1 1 d . . .
N3 N 0.3251(3) 0.8683(2) 0.68413(16) 0.0342(5) Uani 1 1 d . . .
N4 N 0.3558(3) 0.7474(2) 0.58139(16) 0.0384(5) Uani 1 1 d . . .
N5 N 0.6588(3) 0.6914(2) 0.73381(17) 0.0335(5) Uani 1 1 d . . .
N6 N 0.4492(3) 0.6658(2) 0.77248(18) 0.0373(6) Uani 1 1 d . . .
C1 C 0.7888(3) 1.0227(2) 0.7908(2) 0.0358(6) Uani 1 1 d . A .
C2 C 0.9272(4) 1.1257(3) 0.8279(2) 0.0483(8) Uani 1 1 d . . .
C3 C 1.0347(5) 1.2118(4) 0.8548(3) 0.0657(12) Uani 1 1 d . A .
C4 C 1.1632(6) 1.3245(5) 0.8837(3) 0.0687(12) Uani 1 1 d . . .
H4 H 1.1439 1.3814 0.8558 0.082 Uiso 1 1 calc R A .
C5 C 1.2590(8) 1.3662(5) 0.9751(3) 0.089(2) Uani 1 1 d . A .
H5A H 1.2984 1.4479 1.0043 0.107 Uiso 1 1 calc R . .
H5B H 1.2342 1.3177 1.0113 0.107 Uiso 1 1 calc R . .
C6 C 1.3183(6) 1.3291(6) 0.9107(4) 0.0861(18) Uani 1 1 d . A .
H6A H 1.3324 1.2571 0.9061 0.103 Uiso 1 1 calc R . .
H6B H 1.3965 1.3872 0.8991 0.103 Uiso 1 1 calc R . .
C7 C 0.7638(15) 1.0291(11) 0.6432(7) 0.034(2) Uani 0.552(16) 1 d PDU A 1
H7 H 0.8440 1.1065 0.6738 0.041 Uiso 0.552(16) 1 calc PR A 1
C8 C 0.8275(17) 0.9627(13) 0.5901(11) 0.069(4) Uani 0.552(16) 1 d PDU A 1
H8A H 0.9279 0.9687 0.6262 0.103 Uiso 0.552(16) 1 calc PR A 1
H8B H 0.8390 0.9929 0.5428 0.103 Uiso 0.552(16) 1 calc PR A 1
H8C H 0.7568 0.8837 0.5670 0.103 Uiso 0.552(16) 1 calc PR A 1
C9 C 0.6236(11) 1.0377(10) 0.5830(7) 0.062(3) Uani 0.552(16) 1 d PD A 1
H9A H 0.5437 0.9623 0.5529 0.093 Uiso 0.552(16) 1 calc PR A 1
H9B H 0.6533 1.0730 0.5411 0.093 Uiso 0.552(16) 1 calc PR A 1
H9C H 0.5839 1.0834 0.6163 0.093 Uiso 0.552(16) 1 calc PR A 1
C7' C 0.798(3) 1.0300(17) 0.6565(11) 0.046(4) Uani 0.448(16) 1 d PDU A 2
H7' H 0.9122 1.0691 0.6863 0.055 Uiso 0.448(16) 1 calc PR A 2
C8' C 0.757(2) 0.9423(14) 0.5707(9) 0.062(4) Uani 0.448(16) 1 d PDU A 2
H8'1 H 0.8093 0.8908 0.5798 0.093 Uiso 0.448(16) 1 calc PR A 2
H8'2 H 0.7892 0.9802 0.5306 0.093 Uiso 0.448(16) 1 calc PR A 2
H8'3 H 0.6454 0.8997 0.5468 0.093 Uiso 0.448(16) 1 calc PR A 2
C9' C 0.7233(19) 1.1117(12) 0.6341(11) 0.079(6) Uani 0.448(16) 1 d PD A 2
H9'1 H 0.6137 1.0696 0.6009 0.118 Uiso 0.448(16) 1 calc PR A 2
H9'2 H 0.7726 1.1525 0.6002 0.118 Uiso 0.448(16) 1 calc PR A 2
H9'3 H 0.7355 1.1653 0.6870 0.118 Uiso 0.448(16) 1 calc PR A 2
C10 C 0.7884(4) 1.0163(3) 0.93236(19) 0.0442(7) Uani 1 1 d . A .
H10 H 0.9026 1.0522 0.9489 0.053 Uiso 1 1 calc R . .
C11 C 0.7322(7) 1.1040(5) 0.9667(3) 0.0707(14) Uani 1 1 d . . .
H11A H 0.7482 1.1613 0.9371 0.106 Uiso 1 1 calc R A .
H11B H 0.7894 1.1393 1.0283 0.106 Uiso 1 1 calc R . .
H11C H 0.6224 1.0684 0.9570 0.106 Uiso 1 1 calc R . .
C12 C 0.7515(6) 0.9185(4) 0.9685(2) 0.0633(11) Uani 1 1 d . . .
H12A H 0.6399 0.8815 0.9522 0.095 Uiso 1 1 calc R A .
H12B H 0.7988 0.9461 1.0311 0.095 Uiso 1 1 calc R . .
H12C H 0.7921 0.8645 0.9456 0.095 Uiso 1 1 calc R . .
C13 C 0.2733(3) 0.8043(3) 0.60294(18) 0.0334(5) Uani 1 1 d . A .
C14 C 0.1356(4) 0.8000(3) 0.54099(19) 0.0397(6) Uani 1 1 d . . .
C15 C 0.0262(4) 0.7983(3) 0.4889(2) 0.0436(7) Uani 1 1 d . A .
C16 C -0.1038(4) 0.7957(4) 0.4227(2) 0.0490(8) Uani 1 1 d . . .
H16 H -0.1192 0.8681 0.4279 0.059 Uiso 1 1 calc R A .
C17 C -0.1465(5) 0.7232(4) 0.3336(2) 0.0524(9) Uani 1 1 d . A .
H17A H -0.1837 0.7517 0.2857 0.063 Uiso 1 1 calc R . .
H17B H -0.0855 0.6776 0.3236 0.063 Uiso 1 1 calc R . .
C18 C -0.2440(5) 0.6929(6) 0.3830(3) 0.0804(17) Uani 1 1 d . A .
H18A H -0.2456 0.6277 0.4041 0.096 Uiso 1 1 calc R . .
H18B H -0.3437 0.7016 0.3663 0.096 Uiso 1 1 calc R . .
C19 C 0.2573(4) 0.9472(3) 0.7107(2) 0.0404(7) Uani 1 1 d . A .
H19 H 0.1477 0.9189 0.6721 0.048 Uiso 1 1 calc R . .
C20 C 0.3443(7) 1.0617(4) 0.7043(4) 0.0715(13) Uani 1 1 d . . .
H20A H 0.4526 1.0889 0.7406 0.107 Uiso 1 1 calc R A .
H20B H 0.2997 1.1148 0.7234 0.107 Uiso 1 1 calc R . .
H20C H 0.3368 1.0551 0.6446 0.107 Uiso 1 1 calc R . .
C21 C 0.2627(5) 0.9565(4) 0.8016(2) 0.0541(9) Uani 1 1 d . . .
H21A H 0.2033 0.8829 0.8045 0.081 Uiso 1 1 calc R A .
H21B H 0.2187 1.0106 0.8197 0.081 Uiso 1 1 calc R . .
H21C H 0.3697 0.9821 0.8396 0.081 Uiso 1 1 calc R . .
C22 C 0.300(2) 0.6606(17) 0.4982(12) 0.054(6) Uani 0.48(4) 1 d PDU A 1
H22 H 0.2079 0.6660 0.4588 0.065 Uiso 0.48(4) 1 calc PR A 1
C23 C 0.256(5) 0.5456(13) 0.5095(19) 0.130(14) Uani 0.48(4) 1 d PD A 1
H23A H 0.2094 0.4886 0.4532 0.195 Uiso 0.48(4) 1 calc PR A 1
H23B H 0.1822 0.5359 0.5395 0.195 Uiso 0.48(4) 1 calc PR A 1
H23C H 0.3481 0.5374 0.5432 0.195 Uiso 0.48(4) 1 calc PR A 1
C24 C 0.425(2) 0.6787(15) 0.4594(10) 0.064(4) Uani 0.48(4) 1 d PDU A 1
H24A H 0.5201 0.6851 0.5015 0.096 Uiso 0.48(4) 1 calc PR A 1
H24B H 0.4421 0.7479 0.4431 0.096 Uiso 0.48(4) 1 calc PR A 1
H24C H 0.3934 0.6149 0.4085 0.096 Uiso 0.48(4) 1 calc PR A 1
C22' C 0.3013(18) 0.6697(13) 0.4966(14) 0.042(4) Uani 0.52(4) 1 d PDU A 2
H22' H 0.2598 0.7037 0.4529 0.050 Uiso 0.52(4) 1 calc PR A 2
C23' C 0.1775(17) 0.5625(11) 0.4902(10) 0.071(4) Uani 0.52(4) 1 d PD A 2
H23D H 0.2222 0.5242 0.5275 0.107 Uiso 0.52(4) 1 calc PR A 2
H23E H 0.1317 0.5134 0.4308 0.107 Uiso 0.52(4) 1 calc PR A 2
H23F H 0.0979 0.5800 0.5081 0.107 Uiso 0.52(4) 1 calc PR A 2
C24' C 0.4340(16) 0.6429(19) 0.4812(15) 0.078(5) Uani 0.52(4) 1 d PDU A 2
H24D H 0.5206 0.7130 0.4925 0.117 Uiso 0.52(4) 1 calc PR A 2
H24E H 0.4013 0.5972 0.4216 0.117 Uiso 0.52(4) 1 calc PR A 2
H24F H 0.4658 0.6013 0.5197 0.117 Uiso 0.52(4) 1 calc PR A 2
C25 C 0.5603(3) 0.6318(2) 0.76485(18) 0.0314(5) Uani 1 1 d . A .
C26 C 0.5774(3) 0.5346(3) 0.7879(2) 0.0362(6) Uani 1 1 d . . .
C27 C 0.6081(4) 0.4599(3) 0.8061(3) 0.0490(8) Uani 1 1 d . A .
C28 C 0.6568(7) 0.3739(4) 0.8305(5) 0.0853(18) Uani 1 1 d . . .
H28 H 0.5801 0.3140 0.8425 0.102 Uiso 1 1 calc R A .
C29 C 0.7624(14) 0.3408(10) 0.7969(10) 0.175(6) Uani 1 1 d . A .
H29A H 0.7490 0.2608 0.7852 0.210 Uiso 1 1 calc R . .
H29B H 0.7956 0.3766 0.7554 0.210 Uiso 1 1 calc R . .
C30 C 0.8217(11) 0.4075(8) 0.8838(8) 0.151(5) Uani 1 1 d . A .
H30A H 0.8916 0.4868 0.8985 0.182 Uiso 1 1 calc R . .
H30B H 0.8449 0.3707 0.9284 0.182 Uiso 1 1 calc R . .
C31 C 0.7976(3) 0.6713(3) 0.7340(2) 0.0339(6) Uani 1 1 d . A .
H31 H 0.7720 0.5885 0.7161 0.041 Uiso 1 1 calc R . .
C32 C 0.9199(4) 0.7248(3) 0.8237(2) 0.0464(8) Uani 1 1 d . . .
H32A H 0.9440 0.8058 0.8418 0.070 Uiso 1 1 calc R A .
H32B H 1.0130 0.7120 0.8227 0.070 Uiso 1 1 calc R . .
H32C H 0.8810 0.6910 0.8639 0.070 Uiso 1 1 calc R . .
C33 C 0.8552(4) 0.7210(3) 0.6701(2) 0.0462(8) Uani 1 1 d . . .
H33A H 0.7772 0.6833 0.6127 0.069 Uiso 1 1 calc R A .
H33B H 0.9502 0.7104 0.6706 0.069 Uiso 1 1 calc R . .
H33C H 0.8754 0.8014 0.6858 0.069 Uiso 1 1 calc R . .
C34 C 0.3262(4) 0.5990(3) 0.7968(2) 0.0429(7) Uani 1 1 d . A .
H34 H 0.3350 0.5254 0.7975 0.052 Uiso 1 1 calc R . .
C35 C 0.3400(5) 0.6621(6) 0.8855(3) 0.0766(16) Uani 1 1 d . . .
H35A H 0.4379 0.6726 0.9273 0.115 Uiso 1 1 calc R A .
H35B H 0.2550 0.6189 0.9009 0.115 Uiso 1 1 calc R . .
H35C H 0.3359 0.7357 0.8854 0.115 Uiso 1 1 calc R . .
C36 C 0.1727(4) 0.5784(3) 0.7320(3) 0.0494(8) Uani 1 1 d . . .
H36A H 0.1672 0.6506 0.7283 0.074 Uiso 1 1 calc R A .
H36B H 0.0897 0.5381 0.7501 0.074 Uiso 1 1 calc R . .
H36C H 0.1618 0.5333 0.6758 0.074 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
Ho N5 2.342(2) . ?
Ho N3 2.348(2) . ?
Ho N2 2.351(3) . ?
Ho N4 2.353(3) . ?
Ho N1 2.359(3) . ?
Ho N6 2.383(3) . ?
Ho C13 2.755(3) . ?
Ho C1 2.756(3) . ?
Ho C25 2.773(3) . ?
N1 C1 1.312(4) . ?
N1 C7' 1.42(3) . ?
N1 C7 1.480(14) . ?
N2 C1 1.327(4) . ?
N2 C10 1.460(4) . ?
N3 C13 1.333(4) . ?
N3 C19 1.458(4) . ?
N4 C13 1.331(4) . ?
N4 C22' 1.44(2) . ?
N4 C22 1.472(18) . ?
N5 C25 1.333(4) . ?
N5 C31 1.461(3) . ?
N6 C25 1.324(3) . ?
N6 C34 1.461(4) . ?
C1 C2 1.461(5) . ?
C2 C3 1.181(6) . ?
C3 C4 1.496(7) . ?
C4 C6 1.441(8) . ?
C4 C5 1.470(7) . ?
C5 C6 1.440(9) . ?
C7 C8 1.513(11) . ?
C7 C9 1.529(11) . ?
C7' C9' 1.530(14) . ?
C7' C8' 1.536(13) . ?
C10 C11 1.508(6) . ?
C10 C12 1.517(6) . ?
C13 C14 1.449(4) . ?
C14 C15 1.185(4) . ?
C15 C16 1.443(5) . ?
C16 C18 1.469(7) . ?
C16 C17 1.492(5) . ?
C17 C18 1.445(7) . ?
C19 C21 1.510(5) . ?
C19 C20 1.521(6) . ?
C22 C23 1.503(13) . ?
C22 C24 1.514(13) . ?
C22' C23' 1.506(12) . ?
C22' C24' 1.518(11) . ?
C25 C26 1.453(4) . ?
C26 C27 1.184(5) . ?
C27 C28 1.446(5) . ?
C28 C29 1.441(12) . ?
C28 C30 1.497(10) . ?
C29 C30 1.416(16) . ?
C31 C33 1.513(5) . ?
C31 C32 1.528(5) . ?
C34 C36 1.514(5) . ?
C34 C35 1.520(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
N5 Ho N3 153.10(10) . . ?
N5 Ho N2 98.77(10) . . ?
N3 Ho N2 103.76(10) . . ?
N5 Ho N4 106.03(10) . . ?
N3 Ho N4 57.74(9) . . ?
N2 Ho N4 150.92(10) . . ?
N5 Ho N1 104.51(10) . . ?
N3 Ho N1 100.01(11) . . ?
N2 Ho N1 57.08(9) . . ?
N4 Ho N1 101.28(11) . . ?
N5 Ho N6 57.14(8) . . ?
N3 Ho N6 101.51(9) . . ?
N2 Ho N6 107.47(10) . . ?
N4 Ho N6 98.74(11) . . ?
N1 Ho N6 156.20(10) . . ?
N5 Ho C13 131.91(10) . . ?
N3 Ho C13 28.89(9) . . ?
N2 Ho C13 129.31(10) . . ?
N4 Ho C13 28.85(9) . . ?
N1 Ho C13 101.97(10) . . ?
N6 Ho C13 101.78(9) . . ?
N5 Ho C1 102.01(9) . . ?
N3 Ho C1 104.81(10) . . ?
N2 Ho C1 28.74(9) . . ?
N4 Ho C1 127.90(11) . . ?
N1 Ho C1 28.39(9) . . ?
N6 Ho C1 133.32(10) . . ?
C13 Ho C1 119.61(10) . . ?
N5 Ho C25 28.66(8) . . ?
N3 Ho C25 128.45(9) . . ?
N2 Ho C25 104.65(9) . . ?
N4 Ho C25 104.39(10) . . ?
N1 Ho C25 131.54(10) . . ?
N6 Ho C25 28.49(8) . . ?
C13 Ho C25 119.97(9) . . ?
C1 Ho C25 120.41(9) . . ?
C1 N1 C7' 116.5(8) . . ?
C1 N1 C7 124.7(6) . . ?
C7' N1 C7 13.6(9) . . ?
C1 N1 Ho 92.86(19) . . ?
C7' N1 Ho 150.4(8) . . ?
C7 N1 Ho 141.5(5) . . ?
C1 N2 C10 120.7(3) . . ?
C1 N2 Ho 92.83(18) . . ?
C10 N2 Ho 145.6(2) . . ?
C13 N3 C19 120.9(3) . . ?
C13 N3 Ho 92.74(18) . . ?
C19 N3 Ho 144.9(2) . . ?
C13 N4 C22' 120.3(7) . . ?
C13 N4 C22 122.4(9) . . ?
C22' N4 C22 4.7(14) . . ?
C13 N4 Ho 92.59(18) . . ?
C22' N4 Ho 146.9(7) . . ?
C22 N4 Ho 144.0(9) . . ?
C25 N5 C31 121.1(2) . . ?
C25 N5 Ho 93.91(17) . . ?
C31 N5 Ho 143.8(2) . . ?
C25 N6 C34 120.5(3) . . ?
C25 N6 Ho 92.33(17) . . ?
C34 N6 Ho 146.68(19) . . ?
N1 C1 N2 117.0(3) . . ?
N1 C1 C2 120.9(3) . . ?
N2 C1 C2 122.0(3) . . ?
N1 C1 Ho 58.75(16) . . ?
N2 C1 Ho 58.43(16) . . ?
C2 C1 Ho 176.1(2) . . ?
C3 C2 C1 176.1(5) . . ?
C2 C3 C4 175.2(6) . . ?
C6 C4 C5 59.3(4) . . ?
C6 C4 C3 117.8(5) . . ?
C5 C4 C3 116.0(5) . . ?
C6 C5 C4 59.3(4) . . ?
C5 C6 C4 61.4(4) . . ?
N1 C7 C8 110.0(9) . . ?
N1 C7 C9 112.1(9) . . ?
C8 C7 C9 108.6(9) . . ?
N1 C7' C9' 107.4(13) . . ?
N1 C7' C8' 108.1(15) . . ?
C9' C7' C8' 105.3(13) . . ?
N2 C10 C11 111.0(3) . . ?
N2 C10 C12 108.6(3) . . ?
C11 C10 C12 112.2(4) . . ?
N4 C13 N3 116.9(3) . . ?
N4 C13 C14 122.0(3) . . ?
N3 C13 C14 121.1(3) . . ?
N4 C13 Ho 58.55(15) . . ?
N3 C13 Ho 58.37(15) . . ?
C14 C13 Ho 178.0(2) . . ?
C15 C14 C13 177.7(4) . . ?
C14 C15 C16 177.5(3) . . ?
C15 C16 C18 120.0(4) . . ?
C15 C16 C17 118.5(3) . . ?
C18 C16 C17 58.4(3) . . ?
C18 C17 C16 60.0(3) . . ?
C17 C18 C16 61.6(3) . . ?
N3 C19 C21 109.5(3) . . ?
N3 C19 C20 109.8(3) . . ?
C21 C19 C20 110.2(4) . . ?
N4 C22 C23 110.4(13) . . ?
N4 C22 C24 109.6(13) . . ?
C23 C22 C24 109.0(13) . . ?
N4 C22' C23' 109.6(12) . . ?
N4 C22' C24' 108.8(13) . . ?
C23' C22' C24' 108.7(12) . . ?
N6 C25 N5 116.6(3) . . ?
N6 C25 C26 123.3(3) . . ?
N5 C25 C26 120.1(2) . . ?
N6 C25 Ho 59.18(15) . . ?
N5 C25 Ho 57.43(15) . . ?
C26 C25 Ho 177.5(2) . . ?
C27 C26 C25 172.3(3) . . ?
C26 C27 C28 176.0(4) . . ?
C29 C28 C27 120.1(6) . . ?
C29 C28 C30 57.6(7) . . ?
C27 C28 C30 118.2(5) . . ?
C30 C29 C28 63.2(7) . . ?
C29 C30 C28 59.2(6) . . ?
N5 C31 C33 108.2(3) . . ?
N5 C31 C32 110.2(3) . . ?
C33 C31 C32 110.7(3) . . ?
N6 C34 C36 109.0(3) . . ?
N6 C34 C35 109.3(3) . . ?
C36 C34 C35 110.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 Ho N1 C1 -88.5(2) . . . . ?
N3 Ho N1 C1 102.7(2) . . . . ?
N2 Ho N1 C1 2.69(18) . . . . ?
N4 Ho N1 C1 161.5(2) . . . . ?
N6 Ho N1 C1 -51.7(3) . . . . ?
C13 Ho N1 C1 132.1(2) . . . . ?
C25 Ho N1 C1 -77.5(2) . . . . ?
N5 Ho N1 C7' 84.8(13) . . . . ?
N3 Ho N1 C7' -84.1(13) . . . . ?
N2 Ho N1 C7' 175.9(13) . . . . ?
N4 Ho N1 C7' -25.3(13) . . . . ?
N6 Ho N1 C7' 121.5(13) . . . . ?
C13 Ho N1 C7' -54.7(13) . . . . ?
C1 Ho N1 C7' 173.2(14) . . . . ?
C25 Ho N1 C7' 95.8(13) . . . . ?
N5 Ho N1 C7 103.4(7) . . . . ?
N3 Ho N1 C7 -65.5(7) . . . . ?
N2 Ho N1 C7 -165.5(7) . . . . ?
N4 Ho N1 C7 -6.7(7) . . . . ?
N6 Ho N1 C7 140.1(7) . . . . ?
C13 Ho N1 C7 -36.1(7) . . . . ?
C1 Ho N1 C7 -168.2(8) . . . . ?
C25 Ho N1 C7 114.4(7) . . . . ?
N5 Ho N2 C1 99.00(19) . . . . ?
N3 Ho N2 C1 -95.8(2) . . . . ?
N4 Ho N2 C1 -49.5(3) . . . . ?
N1 Ho N2 C1 -2.66(18) . . . . ?
N6 Ho N2 C1 157.20(18) . . . . ?
C13 Ho N2 C1 -80.5(2) . . . . ?
C25 Ho N2 C1 127.68(19) . . . . ?
N5 Ho N2 C10 -68.5(4) . . . . ?
N3 Ho N2 C10 96.7(4) . . . . ?
N4 Ho N2 C10 143.1(4) . . . . ?
N1 Ho N2 C10 -170.1(4) . . . . ?
N6 Ho N2 C10 -10.3(4) . . . . ?
C13 Ho N2 C10 112.0(4) . . . . ?
C1 Ho N2 C10 -167.5(5) . . . . ?
C25 Ho N2 C10 -39.8(4) . . . . ?
N5 Ho N3 C13 -58.9(3) . . . . ?
N2 Ho N3 C13 155.01(18) . . . . ?
N4 Ho N3 C13 -0.42(18) . . . . ?
N1 Ho N3 C13 96.67(19) . . . . ?
N6 Ho N3 C13 -93.57(19) . . . . ?
C1 Ho N3 C13 125.35(19) . . . . ?
C25 Ho N3 C13 -83.2(2) . . . . ?
N5 Ho N3 C19 137.0(4) . . . . ?
N2 Ho N3 C19 -9.1(4) . . . . ?
N4 Ho N3 C19 -164.5(4) . . . . ?
N1 Ho N3 C19 -67.4(4) . . . . ?
N6 Ho N3 C19 102.3(4) . . . . ?
C13 Ho N3 C19 -164.1(5) . . . . ?
C1 Ho N3 C19 -38.7(4) . . . . ?
C25 Ho N3 C19 112.7(4) . . . . ?
N5 Ho N4 C13 156.76(19) . . . . ?
N3 Ho N4 C13 0.42(18) . . . . ?
N2 Ho N4 C13 -55.8(3) . . . . ?
N1 Ho N4 C13 -94.4(2) . . . . ?
N6 Ho N4 C13 98.6(2) . . . . ?
C1 Ho N4 C13 -83.4(2) . . . . ?
C25 Ho N4 C13 127.08(19) . . . . ?
N5 Ho N4 C22' -16.7(11) . . . . ?
N3 Ho N4 C22' -173.1(11) . . . . ?
N2 Ho N4 C22' 130.7(11) . . . . ?
N1 Ho N4 C22' 92.1(11) . . . . ?
N6 Ho N4 C22' -74.9(11) . . . . ?
C13 Ho N4 C22' -173.5(12) . . . . ?
C1 Ho N4 C22' 103.1(11) . . . . ?
C25 Ho N4 C22' -46.4(11) . . . . ?
N5 Ho N4 C22 -10.1(13) . . . . ?
N3 Ho N4 C22 -166.5(13) . . . . ?
N2 Ho N4 C22 137.3(13) . . . . ?
N1 Ho N4 C22 98.7(13) . . . . ?
N6 Ho N4 C22 -68.3(13) . . . . ?
C13 Ho N4 C22 -166.9(13) . . . . ?
C1 Ho N4 C22 109.7(13) . . . . ?
C25 Ho N4 C22 -39.8(13) . . . . ?
N3 Ho N5 C25 -42.2(3) . . . . ?
N2 Ho N5 C25 104.56(19) . . . . ?
N4 Ho N5 C25 -90.8(2) . . . . ?
N1 Ho N5 C25 162.68(18) . . . . ?
N6 Ho N5 C25 -0.63(17) . . . . ?
C13 Ho N5 C25 -76.0(2) . . . . ?
C1 Ho N5 C25 133.60(18) . . . . ?
N3 Ho N5 C31 152.1(3) . . . . ?
N2 Ho N5 C31 -61.2(4) . . . . ?
N4 Ho N5 C31 103.5(4) . . . . ?
N1 Ho N5 C31 -3.0(4) . . . . ?
N6 Ho N5 C31 -166.4(4) . . . . ?
C13 Ho N5 C31 118.3(3) . . . . ?
C1 Ho N5 C31 -32.1(4) . . . . ?
C25 Ho N5 C31 -165.7(5) . . . . ?
N5 Ho N6 C25 0.63(17) . . . . ?
N3 Ho N6 C25 162.80(18) . . . . ?
N2 Ho N6 C25 -88.6(2) . . . . ?
N4 Ho N6 C25 104.12(19) . . . . ?
N1 Ho N6 C25 -42.9(3) . . . . ?
C13 Ho N6 C25 133.29(19) . . . . ?
C1 Ho N6 C25 -73.8(2) . . . . ?
N5 Ho N6 C34 -170.3(5) . . . . ?
N3 Ho N6 C34 -8.1(4) . . . . ?
N2 Ho N6 C34 100.4(4) . . . . ?
N4 Ho N6 C34 -66.8(4) . . . . ?
N1 Ho N6 C34 146.2(4) . . . . ?
C13 Ho N6 C34 -37.6(4) . . . . ?
C1 Ho N6 C34 115.3(4) . . . . ?
C25 Ho N6 C34 -170.9(5) . . . . ?
C7' N1 C1 N2 179.2(7) . . . . ?
C7 N1 C1 N2 166.6(6) . . . . ?
Ho N1 C1 N2 -4.5(3) . . . . ?
C7' N1 C1 C2 -0.9(8) . . . . ?
C7 N1 C1 C2 -13.5(7) . . . . ?
Ho N1 C1 C2 175.4(3) . . . . ?
C7' N1 C1 Ho -176.3(7) . . . . ?
C7 N1 C1 Ho 171.1(6) . . . . ?
C10 N2 C1 N1 176.3(3) . . . . ?
Ho N2 C1 N1 4.5(3) . . . . ?
C10 N2 C1 C2 -3.6(5) . . . . ?
Ho N2 C1 C2 -175.4(3) . . . . ?
C10 N2 C1 Ho 171.8(3) . . . . ?
N5 Ho C1 N1 98.4(2) . . . . ?
N3 Ho C1 N1 -83.6(2) . . . . ?
N2 Ho C1 N1 -175.3(3) . . . . ?
N4 Ho C1 N1 -23.2(2) . . . . ?
N6 Ho C1 N1 154.18(19) . . . . ?
C13 Ho C1 N1 -56.7(2) . . . . ?
C25 Ho C1 N1 122.1(2) . . . . ?
N5 Ho C1 N2 -86.4(2) . . . . ?
N3 Ho C1 N2 91.7(2) . . . . ?
N4 Ho C1 N2 152.09(18) . . . . ?
N1 Ho C1 N2 175.3(3) . . . . ?
N6 Ho C1 N2 -30.5(2) . . . . ?
C13 Ho C1 N2 118.63(19) . . . . ?
C25 Ho C1 N2 -62.6(2) . . . . ?
N5 Ho C1 C2 12(4) . . . . ?
N3 Ho C1 C2 -170(4) . . . . ?
N2 Ho C1 C2 98(4) . . . . ?
N4 Ho C1 C2 -110(4) . . . . ?
N1 Ho C1 C2 -87(4) . . . . ?
N6 Ho C1 C2 68(4) . . . . ?
C13 Ho C1 C2 -143(4) . . . . ?
C25 Ho C1 C2 36(4) . . . . ?
N1 C1 C2 C3 54(6) . . . . ?
N2 C1 C2 C3 -126(6) . . . . ?
Ho C1 C2 C3 138(5) . . . . ?
C1 C2 C3 C4 -1(11) . . . . ?
C2 C3 C4 C6 -147(6) . . . . ?
C2 C3 C4 C5 146(6) . . . . ?
C3 C4 C5 C6 108.4(6) . . . . ?
C3 C4 C6 C5 -105.2(5) . . . . ?
C1 N1 C7 C8 118.8(10) . . . . ?
C7' N1 C7 C8 63(4) . . . . ?
Ho N1 C7 C8 -75.6(14) . . . . ?
C1 N1 C7 C9 -120.2(8) . . . . ?
C7' N1 C7 C9 -176(5) . . . . ?
Ho N1 C7 C9 45.4(12) . . . . ?
C1 N1 C7' C9' -90.9(12) . . . . ?
C7 N1 C7' C9' 39(4) . . . . ?
Ho N1 C7' C9' 96.7(16) . . . . ?
C1 N1 C7' C8' 156.0(11) . . . . ?
C7 N1 C7' C8' -74(4) . . . . ?
Ho N1 C7' C8' -16(2) . . . . ?
C1 N2 C10 C11 88.5(5) . . . . ?
Ho N2 C10 C11 -106.1(5) . . . . ?
C1 N2 C10 C12 -147.7(3) . . . . ?
Ho N2 C10 C12 17.7(5) . . . . ?
C22' N4 C13 N3 175.2(7) . . . . ?
C22 N4 C13 N3 170.2(10) . . . . ?
Ho N4 C13 N3 -0.7(3) . . . . ?
C22' N4 C13 C14 -6.4(8) . . . . ?
C22 N4 C13 C14 -11.4(10) . . . . ?
Ho N4 C13 C14 177.7(3) . . . . ?
C22' N4 C13 Ho 175.9(7) . . . . ?
C22 N4 C13 Ho 170.9(10) . . . . ?
C19 N3 C13 N4 170.1(3) . . . . ?
Ho N3 C13 N4 0.7(3) . . . . ?
C19 N3 C13 C14 -8.3(5) . . . . ?
Ho N3 C13 C14 -177.7(3) . . . . ?
C19 N3 C13 Ho 169.4(3) . . . . ?
N5 Ho C13 N4 -30.6(2) . . . . ?
N3 Ho C13 N4 -179.3(3) . . . . ?
N2 Ho C13 N4 148.70(19) . . . . ?
N1 Ho C13 N4 91.7(2) . . . . ?
N6 Ho C13 N4 -86.8(2) . . . . ?
C1 Ho C13 N4 115.6(2) . . . . ?
C25 Ho C13 N4 -63.1(2) . . . . ?
N5 Ho C13 N3 148.63(18) . . . . ?
N2 Ho C13 N3 -32.0(2) . . . . ?
N4 Ho C13 N3 179.3(3) . . . . ?
N1 Ho C13 N3 -89.0(2) . . . . ?
N6 Ho C13 N3 92.52(19) . . . . ?
C1 Ho C13 N3 -65.1(2) . . . . ?
C25 Ho C13 N3 116.14(19) . . . . ?
N5 Ho C13 C14 -136(7) . . . . ?
N3 Ho C13 C14 75(7) . . . . ?
N2 Ho C13 C14 43(7) . . . . ?
N4 Ho C13 C14 -106(7) . . . . ?
N1 Ho C13 C14 -14(7) . . . . ?
N6 Ho C13 C14 167(7) . . . . ?
C1 Ho C13 C14 10(7) . . . . ?
C25 Ho C13 C14 -169(7) . . . . ?
N4 C13 C14 C15 -66(10) . . . . ?
N3 C13 C14 C15 113(10) . . . . ?
Ho C13 C14 C15 39(15) . . . . ?
C13 C14 C15 C16 32(19) . . . . ?
C14 C15 C16 C18 103(10) . . . . ?
C14 C15 C16 C17 35(10) . . . . ?
C15 C16 C17 C18 109.5(5) . . . . ?
C15 C16 C18 C17 -107.0(4) . . . . ?
C13 N3 C19 C21 147.1(3) . . . . ?
Ho N3 C19 C21 -51.5(5) . . . . ?
C13 N3 C19 C20 -91.7(4) . . . . ?
Ho N3 C19 C20 69.7(5) . . . . ?
C13 N4 C22 C23 -107.0(19) . . . . ?
C22' N4 C22 C23 -172(16) . . . . ?
Ho N4 C22 C23 57(3) . . . . ?
C13 N4 C22 C24 133.0(15) . . . . ?
C22' N4 C22 C24 68(15) . . . . ?
Ho N4 C22 C24 -63(3) . . . . ?
C13 N4 C22' C23' -77.3(14) . . . . ?
C22 N4 C22' C23' 41(14) . . . . ?
Ho N4 C22' C23' 95.1(13) . . . . ?
C13 N4 C22' C24' 163.9(14) . . . . ?
C22 N4 C22' C24' -78(15) . . . . ?
Ho N4 C22' C24' -24(2) . . . . ?
C34 N6 C25 N5 173.2(3) . . . . ?
Ho N6 C25 N5 -1.0(3) . . . . ?
C34 N6 C25 C26 -6.4(5) . . . . ?
Ho N6 C25 C26 179.4(3) . . . . ?
C34 N6 C25 Ho 174.2(3) . . . . ?
C31 N5 C25 N6 171.3(3) . . . . ?
Ho N5 C25 N6 1.1(3) . . . . ?
C31 N5 C25 C26 -9.1(4) . . . . ?
Ho N5 C25 C26 -179.3(2) . . . . ?
C31 N5 C25 Ho 170.2(3) . . . . ?
N5 Ho C25 N6 -178.9(3) . . . . ?
N3 Ho C25 N6 -21.7(2) . . . . ?
N2 Ho C25 N6 99.7(2) . . . . ?
N4 Ho C25 N6 -81.7(2) . . . . ?
N1 Ho C25 N6 158.46(18) . . . . ?
C13 Ho C25 N6 -55.3(2) . . . . ?
C1 Ho C25 N6 125.90(19) . . . . ?
N3 Ho C25 N5 157.18(18) . . . . ?
N2 Ho C25 N5 -81.39(19) . . . . ?
N4 Ho C25 N5 97.17(19) . . . . ?
N1 Ho C25 N5 -22.6(2) . . . . ?
N6 Ho C25 N5 178.9(3) . . . . ?
C13 Ho C25 N5 123.55(18) . . . . ?
C1 Ho C25 N5 -55.2(2) . . . . ?
N5 Ho C25 C26 13(5) . . . . ?
N3 Ho C25 C26 170(5) . . . . ?
N2 Ho C25 C26 -68(5) . . . . ?
N4 Ho C25 C26 110(5) . . . . ?
N1 Ho C25 C26 -9(5) . . . . ?
N6 Ho C25 C26 -168(5) . . . . ?
C13 Ho C25 C26 137(5) . . . . ?
C1 Ho C25 C26 -42(5) . . . . ?
N6 C25 C26 C27 -166(3) . . . . ?
N5 C25 C26 C27 14(3) . . . . ?
Ho C25 C26 C27 1(7) . . . . ?
C25 C26 C27 C28 25(9) . . . . ?
C26 C27 C28 C29 -57(8) . . . . ?
C26 C27 C28 C30 10(8) . . . . ?
C27 C28 C29 C30 106.2(8) . . . . ?
C27 C28 C30 C29 -109.5(8) . . . . ?
C25 N5 C31 C33 161.3(3) . . . . ?
Ho N5 C31 C33 -35.4(5) . . . . ?
C25 N5 C31 C32 -77.6(4) . . . . ?
Ho N5 C31 C32 85.7(4) . . . . ?
C25 N6 C34 C36 -127.4(3) . . . . ?
Ho N6 C34 C36 42.0(6) . . . . ?
C25 N6 C34 C35 112.3(4) . . . . ?
Ho N6 C34 C35 -78.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.21
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         2.465
_refine_diff_density_min         -1.743
_refine_diff_density_rms         0.107

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ip376
_database_code_depnum_ccdc_archive 'CCDC 1050916'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H28 N2'
_chemical_formula_weight         308.45

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.7257(19)
_cell_length_b                   10.383(2)
_cell_length_c                   10.558(2)
_cell_angle_alpha                70.77(3)
_cell_angle_beta                 65.92(3)
_cell_angle_gamma                70.83(3)
_cell_volume                     895.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    13836
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      29.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7657
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3625
_reflns_number_gt                2823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0793P)²+0.1452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3625
_refine_ls_number_parameters     267
_refine_ls_number_restraints     157
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.227
_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 0.0505(2) 0.24196(17) 0.56925(18) 0.0459(5) Uani 1 1 d . . .
H1 H 0.025(3) 0.303(3) 0.502(3) 0.058(7) Uiso 1 1 d . . .
C1 C 0.1466(2) 0.11751(18) 0.54171(19) 0.0318(4) Uani 1 1 d . A .
C2 C 0.1948(2) 0.11298(18) 0.39354(19) 0.0338(4) Uani 1 1 d . . .
C3 C 0.2281(2) 0.11473(17) 0.27086(19) 0.0324(4) Uani 1 1 d . . .
C4 C 0.2657(2) 0.11620(16) 0.12403(18) 0.0298(4) Uani 1 1 d . . .
C5 C 0.3856(2) 0.17557(19) 0.0184(2) 0.0370(4) Uani 1 1 d . . .
H5 H 0.4432 0.2160 0.0429 0.044 Uiso 1 1 calc R . .
C6 C 0.4204(2) 0.1755(2) -0.1219(2) 0.0429(5) Uani 1 1 d . . .
H6 H 0.5013 0.2169 -0.1941 0.051 Uiso 1 1 calc R . .
C7 C 0.3382(2) 0.1155(2) -0.1583(2) 0.0431(5) Uani 1 1 d . . .
H7 H 0.3634 0.1150 -0.2551 0.052 Uiso 1 1 calc R . .
C8 C 0.2197(2) 0.0563(2) -0.0541(2) 0.0400(4) Uani 1 1 d . . .
H8 H 0.1636 0.0148 -0.0794 0.048 Uiso 1 1 calc R . .
C9 C 0.1820(2) 0.05706(17) 0.0867(2) 0.0339(4) Uani 1 1 d . . .
H9 H 0.0994 0.0174 0.1580 0.041 Uiso 1 1 calc R . .
C10 C -0.0189(2) 0.27812(17) 0.70702(19) 0.0352(4) Uani 1 1 d . . .
H10 H 0.0025 0.1916 0.7803 0.042 Uiso 1 1 calc R . .
C11 C -0.1925(3) 0.3284(2) 0.7437(3) 0.0517(5) Uani 1 1 d . . .
H11A H -0.2361 0.2528 0.7475 0.062 Uiso 1 1 calc R . .
H11B H -0.2161 0.4095 0.6680 0.062 Uiso 1 1 calc R . .
C12 C -0.2682(3) 0.3706(3) 0.8858(3) 0.0686(8) Uani 1 1 d . . .
H12A H -0.3804 0.4083 0.9033 0.082 Uiso 1 1 calc R . .
H12B H -0.2551 0.2870 0.9629 0.082 Uiso 1 1 calc R . .
C13 C -0.1991(4) 0.4795(2) 0.8889(3) 0.0692(8) Uani 1 1 d . . .
H13A H -0.2462 0.5001 0.9848 0.083 Uiso 1 1 calc R . .
H13B H -0.2227 0.5671 0.8193 0.083 Uiso 1 1 calc R . .
C14 C -0.0254(4) 0.4298(2) 0.8534(3) 0.0629(7) Uani 1 1 d . . .
H14A H -0.0019 0.3491 0.9295 0.075 Uiso 1 1 calc R . .
H14B H 0.0176 0.5059 0.8493 0.075 Uiso 1 1 calc R . .
C15 C 0.0507(3) 0.3869(2) 0.7113(2) 0.0436(5) Uani 1 1 d . . .
H15A H 0.0385 0.4706 0.6339 0.052 Uiso 1 1 calc R . .
H15B H 0.1627 0.3486 0.6945 0.052 Uiso 1 1 calc R . .
N2 N 0.18685(18) 0.01863(16) 0.63872(16) 0.0353(4) Uani 1 1 d D . .
C16 C 0.2989(8) -0.1059(7) 0.5957(10) 0.0275(12) Uani 0.629(6) 1 d PDU A 1
H16 H 0.3605 -0.0806 0.4923 0.033 Uiso 0.629(6) 1 calc PR A 1
C17 C 0.2058(4) -0.2084(4) 0.6175(6) 0.0429(10) Uani 0.629(6) 1 d PDU A 1
H17A H 0.1399 -0.1673 0.5568 0.051 Uiso 0.629(6) 1 calc PR A 1
H17B H 0.1378 -0.2281 0.7182 0.051 Uiso 0.629(6) 1 calc PR A 1
C18 C 0.3161(4) -0.3442(4) 0.5787(5) 0.0480(10) Uani 0.629(6) 1 d PDU A 1
H18A H 0.2560 -0.4138 0.5995 0.058 Uiso 0.629(6) 1 calc PR A 1
H18B H 0.3759 -0.3260 0.4755 0.058 Uiso 0.629(6) 1 calc PR A 1
C19 C 0.4266(9) -0.4027(7) 0.6636(10) 0.050(2) Uani 0.629(6) 1 d PDU A 1
H19A H 0.3694 -0.4086 0.7665 0.061 Uiso 0.629(6) 1 calc PR A 1
H19B H 0.4889 -0.4969 0.6493 0.061 Uiso 0.629(6) 1 calc PR A 1
C20 C 0.5278(9) -0.2984(7) 0.6039(10) 0.070(2) Uani 0.629(6) 1 d PDU A 1
H20A H 0.5594 -0.2695 0.4988 0.085 Uiso 0.629(6) 1 calc PR A 1
H20B H 0.6210 -0.3362 0.6327 0.085 Uiso 0.629(6) 1 calc PR A 1
C21 C 0.4069(6) -0.1657(4) 0.6806(6) 0.0421(11) Uani 0.629(6) 1 d PDU A 1
H21A H 0.3512 -0.1998 0.7828 0.051 Uiso 0.629(6) 1 calc PR A 1
H21B H 0.4623 -0.0962 0.6704 0.051 Uiso 0.629(6) 1 calc PR A 1
C16' C 0.2675(13) -0.1244(11) 0.6061(16) 0.033(3) Uani 0.371(6) 1 d PDU A 2
H16' H 0.2750 -0.1198 0.5074 0.040 Uiso 0.371(6) 1 calc PR A 2
C17' C 0.1955(6) -0.2447(6) 0.7063(9) 0.0384(15) Uani 0.371(6) 1 d PDU A 2
H17C H 0.0940 -0.2315 0.6974 0.046 Uiso 0.371(6) 1 calc PR A 2
H17D H 0.1768 -0.2429 0.8053 0.046 Uiso 0.371(6) 1 calc PR A 2
C18' C 0.2941(7) -0.3882(6) 0.6794(9) 0.0455(18) Uani 0.371(6) 1 d PDU A 2
H18C H 0.2395 -0.4610 0.7504 0.055 Uiso 0.371(6) 1 calc PR A 2
H18D H 0.3038 -0.3930 0.5840 0.055 Uiso 0.371(6) 1 calc PR A 2
C19' C 0.4511(14) -0.4209(13) 0.6870(17) 0.047(3) Uani 0.371(6) 1 d PDU A 2
H19C H 0.4492 -0.4746 0.7842 0.056 Uiso 0.371(6) 1 calc PR A 2
H19D H 0.5228 -0.4811 0.6200 0.056 Uiso 0.371(6) 1 calc PR A 2
C20' C 0.5073(15) -0.3018(12) 0.6542(12) 0.054(3) Uani 0.371(6) 1 d PDU A 2
H20C H 0.6089 -0.3172 0.5782 0.065 Uiso 0.371(6) 1 calc PR A 2
H20D H 0.5295 -0.3067 0.7394 0.065 Uiso 0.371(6) 1 calc PR A 2
C21' C 0.4315(9) -0.1525(8) 0.6092(11) 0.054(2) Uani 0.371(6) 1 d PDU A 2
H21C H 0.4978 -0.1138 0.5126 0.065 Uiso 0.371(6) 1 calc PR A 2
H21D H 0.4274 -0.1001 0.6743 0.065 Uiso 0.371(6) 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
N1 C1 1.364(2) . ?
N1 C10 1.451(3) . ?
C1 N2 1.275(2) . ?
C1 C2 1.451(2) . ?
C2 C3 1.195(3) . ?
C3 C4 1.436(2) . ?
C4 C5 1.393(3) . ?
C4 C9 1.394(2) . ?
C5 C6 1.379(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.381(3) . ?
C10 C11 1.515(3) . ?
C10 C15 1.515(3) . ?
C11 C12 1.518(4) . ?
C12 C13 1.508(4) . ?
C13 C14 1.516(4) . ?
C14 C15 1.521(3) . ?
N2 C16 1.457(7) . ?
N2 C16' 1.513(11) . ?
C16 C21 1.505(8) . ?
C16 C17 1.519(7) . ?
C17 C18 1.528(4) . ?
C18 C19 1.525(8) . ?
C19 C20 1.510(9) . ?
C20 C21 1.683(8) . ?
C16' C17' 1.506(11) . ?
C16' C21' 1.537(11) . ?
C17' C18' 1.529(7) . ?
C18' C19' 1.480(11) . ?
C19' C20' 1.399(12) . ?
C20' C21' 1.491(11) . ?

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 N1 C10 125.79(15) . . ?
N2 C1 N1 121.93(17) . . ?
N2 C1 C2 125.55(17) . . ?
N1 C1 C2 112.52(15) . . ?
C3 C2 C1 176.65(18) . . ?
C2 C3 C4 179.07(18) . . ?
C5 C4 C9 119.58(16) . . ?
C5 C4 C3 120.70(16) . . ?
C9 C4 C3 119.72(16) . . ?
C6 C5 C4 119.82(17) . . ?
C5 C6 C7 120.42(18) . . ?
C8 C7 C6 120.03(18) . . ?
C7 C8 C9 120.30(17) . . ?
C8 C9 C4 119.84(17) . . ?
N1 C10 C11 110.35(17) . . ?
N1 C10 C15 111.42(16) . . ?
C11 C10 C15 110.87(17) . . ?
C10 C11 C12 111.7(2) . . ?
C13 C12 C11 111.5(2) . . ?
C12 C13 C14 111.3(2) . . ?
C13 C14 C15 111.1(2) . . ?
C10 C15 C14 111.94(18) . . ?
C1 N2 C16 117.4(4) . . ?
C1 N2 C16' 118.2(6) . . ?
C16 N2 C16' 14.3(6) . . ?
N2 C16 C21 111.0(6) . . ?
N2 C16 C17 106.2(5) . . ?
C21 C16 C17 112.1(6) . . ?
C16 C17 C18 109.3(4) . . ?
C19 C18 C17 110.3(4) . . ?
C20 C19 C18 103.8(6) . . ?
C19 C20 C21 100.9(6) . . ?
C16 C21 C20 101.2(5) . . ?
C17' C16' N2 116.6(9) . . ?
C17' C16' C21' 108.6(8) . . ?
N2 C16' C21' 105.5(8) . . ?
C16' C17' C18' 113.8(6) . . ?
C19' C18' C17' 114.6(7) . . ?
C20' C19' C18' 113.3(10) . . ?
C19' C20' C21' 128.1(10) . . ?
C20' C21' C16' 116.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C1 N2 -0.8(3) . . . . ?
C10 N1 C1 C2 179.10(18) . . . . ?
N2 C1 C2 C3 160(3) . . . . ?
N1 C1 C2 C3 -20(3) . . . . ?
C1 C2 C3 C4 -63(13) . . . . ?
C2 C3 C4 C5 167(12) . . . . ?
C2 C3 C4 C9 -13(12) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C6 179.75(16) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C4 -0.9(3) . . . . ?
C5 C4 C9 C8 0.8(2) . . . . ?
C3 C4 C9 C8 -178.96(16) . . . . ?
C1 N1 C10 C11 -126.6(2) . . . . ?
C1 N1 C10 C15 109.8(2) . . . . ?
N1 C10 C11 C12 -178.56(17) . . . . ?
C15 C10 C11 C12 -54.6(2) . . . . ?
C10 C11 C12 C13 55.5(3) . . . . ?
C11 C12 C13 C14 -55.4(3) . . . . ?
C12 C13 C14 C15 55.0(3) . . . . ?
N1 C10 C15 C14 177.83(17) . . . . ?
C11 C10 C15 C14 54.5(2) . . . . ?
C13 C14 C15 C10 -54.8(2) . . . . ?
N1 C1 N2 C16 -175.6(4) . . . . ?
C2 C1 N2 C16 4.5(4) . . . . ?
N1 C1 N2 C16' 168.3(5) . . . . ?
C2 C1 N2 C16' -11.7(5) . . . . ?
C1 N2 C16 C21 143.9(5) . . . . ?
C16' N2 C16 C21 -119(4) . . . . ?
C1 N2 C16 C17 -94.0(6) . . . . ?
C16' N2 C16 C17 3(3) . . . . ?
N2 C16 C17 C18 -178.3(4) . . . . ?
C21 C16 C17 C18 -56.8(7) . . . . ?
C16 C17 C18 C19 55.1(7) . . . . ?
C17 C18 C19 C20 -68.4(7) . . . . ?
C18 C19 C20 C21 75.8(7) . . . . ?
N2 C16 C21 C20 -176.6(5) . . . . ?
C17 C16 C21 C20 64.8(7) . . . . ?
C19 C20 C21 C16 -74.3(7) . . . . ?
C1 N2 C16' C17' -124.6(8) . . . . ?
C16 N2 C16' C17' 145(4) . . . . ?
C1 N2 C16' C21' 114.7(8) . . . . ?
C16 N2 C16' C21' 24(3) . . . . ?
N2 C16' C17' C18' -172.0(7) . . . . ?
C21' C16' C17' C18' -53.0(12) . . . . ?
C16' C17' C18' C19' 57.5(11) . . . . ?
C17' C18' C19' C20' -26.8(15) . . . . ?
C18' C19' C20' C21' -2(2) . . . . ?
C19' C20' C21' C16' 3.7(19) . . . . ?
C17' C16' C21' C20' 23.9(14) . . . . ?
N2 C16' C21' C20' 149.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.044

