# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_120713c
_database_code_depnum_ccdc_archive 'CCDC 916622'
#TrackingRef 'Xie-1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H38 N2 O3'
_chemical_formula_weight         558.69
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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                   9.9120(6)
_cell_length_b                   11.6861(9)
_cell_length_c                   15.4195(11)
_cell_angle_alpha                93.9300(10)
_cell_angle_beta                 104.033(2)
_cell_angle_gamma                103.177(2)
_cell_volume                     1672.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1519
_cell_measurement_theta_min      2.408
_cell_measurement_theta_max      26.055
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9930
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8551
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5829
_reflns_number_gt                2912
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5829
_refine_ls_number_parameters     448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N1 N 0.8916(2) 0.49741(18) 0.61556(13) 0.0419(6) Uani 1 1 d . . .
H1 H 0.9027 0.4580 0.5698 0.050 Uiso 1 1 calc R . .
N2 N 0.5442(2) 0.19168(19) 0.50881(13) 0.0443(6) Uani 1 1 d . . .
H2 H 0.5516 0.1276 0.5318 0.053 Uiso 1 1 calc R . .
O1 O 0.81015(16) 0.25193(15) 0.65735(13) 0.0454(5) Uani 1 1 d . . .
H1A H 0.7663 0.1831 0.6563 0.068 Uiso 1 1 calc R . .
O2 O 1.0608(2) 0.63963(19) 0.52611(14) 0.0766(7) Uani 1 1 d . . .
O3 O 0.3541(2) -0.00900(18) 0.39688(13) 0.0625(6) Uani 1 1 d . . .
C1 C 0.7113(3) 0.3264(2) 0.64664(16) 0.0385(7) Uani 1 1 d . . .
C2 C 0.6220(3) 0.3106(2) 0.71583(17) 0.0372(7) Uani 1 1 d . . .
C3 C 0.4865(3) 0.3321(2) 0.69764(18) 0.0456(7) Uani 1 1 d . . .
H3 H 0.4448 0.3483 0.6405 0.055 Uiso 1 1 calc R . .
C4 C 0.4117(3) 0.3300(3) 0.7640(2) 0.0516(8) Uani 1 1 d . A .
C5 C 0.4782(3) 0.3060(3) 0.84857(19) 0.0552(8) Uani 1 1 d . . .
H5 H 0.4303 0.3049 0.8935 0.066 Uiso 1 1 calc R . .
C6 C 0.6137(3) 0.2834(3) 0.86887(18) 0.0517(8) Uani 1 1 d . B .
C7 C 0.6834(3) 0.2847(2) 0.80079(18) 0.0464(7) Uani 1 1 d . . .
H7 H 0.7729 0.2679 0.8123 0.056 Uiso 1 1 calc R . .
C8 C 0.2607(3) 0.3539(4) 0.7411(3) 0.0726(10) Uani 1 1 d . . .
C9 C 0.2791(8) 0.4859(7) 0.7302(11) 0.119(4) Uani 0.80(2) 1 d P A 1
H9A H 0.1889 0.5057 0.7250 0.178 Uiso 0.80(2) 1 calc PR A 1
H9B H 0.3104 0.5012 0.6770 0.178 Uiso 0.80(2) 1 calc PR A 1
H9C H 0.3494 0.5332 0.7820 0.178 Uiso 0.80(2) 1 calc PR A 1
C10 C 0.1651(8) 0.2758(14) 0.6536(7) 0.116(4) Uani 0.80(2) 1 d P A 1
H10A H 0.0699 0.2873 0.6422 0.175 Uiso 0.80(2) 1 calc PR A 1
H10B H 0.1614 0.1940 0.6597 0.175 Uiso 0.80(2) 1 calc PR A 1
H10C H 0.2045 0.2973 0.6042 0.175 Uiso 0.80(2) 1 calc PR A 1
C11 C 0.1844(8) 0.3277(14) 0.8160(7) 0.117(4) Uani 0.80(2) 1 d P A 1
H11A H 0.2399 0.3780 0.8708 0.176 Uiso 0.80(2) 1 calc PR A 1
H11B H 0.1749 0.2462 0.8255 0.176 Uiso 0.80(2) 1 calc PR A 1
H11C H 0.0908 0.3425 0.7985 0.176 Uiso 0.80(2) 1 calc PR A 1
C9' C 0.166(3) 0.249(4) 0.772(3) 0.100(12) Uani 0.20(2) 1 d P A 2
H9'1 H 0.2084 0.2434 0.8338 0.149 Uiso 0.20(2) 1 calc PR A 2
H9'2 H 0.1594 0.1767 0.7353 0.149 Uiso 0.20(2) 1 calc PR A 2
H9'3 H 0.0718 0.2610 0.7652 0.149 Uiso 0.20(2) 1 calc PR A 2
C10' C 0.273(3) 0.470(3) 0.799(4) 0.109(14) Uani 0.20(2) 1 d P A 2
H10D H 0.1930 0.5013 0.7738 0.164 Uiso 0.20(2) 1 calc PR A 2
H10E H 0.3609 0.5260 0.7992 0.164 Uiso 0.20(2) 1 calc PR A 2
H10F H 0.2738 0.4549 0.8592 0.164 Uiso 0.20(2) 1 calc PR A 2
C11' C 0.199(4) 0.361(5) 0.641(3) 0.105(13) Uani 0.20(2) 1 d P A 2
H11D H 0.1020 0.3687 0.6315 0.157 Uiso 0.20(2) 1 calc PR A 2
H11E H 0.1992 0.2905 0.6058 0.157 Uiso 0.20(2) 1 calc PR A 2
H11F H 0.2563 0.4289 0.6238 0.157 Uiso 0.20(2) 1 calc PR A 2
C12 C 0.6865(4) 0.2582(4) 0.9632(2) 0.0738(10) Uani 1 1 d . . .
C13 C 0.5878(9) 0.2583(10) 1.0287(3) 0.117(4) Uani 0.815(15) 1 d P B 1
H13A H 0.4986 0.1995 1.0040 0.175 Uiso 0.815(15) 1 calc PR B 1
H13B H 0.5691 0.3350 1.0357 0.175 Uiso 0.815(15) 1 calc PR B 1
H13C H 0.6351 0.2404 1.0863 0.175 Uiso 0.815(15) 1 calc PR B 1
C14 C 0.7130(9) 0.1343(6) 0.9564(4) 0.108(3) Uani 0.815(15) 1 d P B 1
H14A H 0.7547 0.1173 1.0156 0.162 Uiso 0.815(15) 1 calc PR B 1
H14B H 0.7774 0.1311 0.9193 0.162 Uiso 0.815(15) 1 calc PR B 1
H14C H 0.6234 0.0766 0.9301 0.162 Uiso 0.815(15) 1 calc PR B 1
C15 C 0.8254(8) 0.3524(10) 1.0034(4) 0.137(4) Uani 0.815(15) 1 d P B 1
H15A H 0.8686 0.3379 1.0630 0.205 Uiso 0.815(15) 1 calc PR B 1
H15B H 0.8055 0.4290 1.0063 0.205 Uiso 0.815(15) 1 calc PR B 1
H15C H 0.8900 0.3501 0.9663 0.205 Uiso 0.815(15) 1 calc PR B 1
C13' C 0.846(3) 0.258(4) 0.9719(17) 0.107(13) Uani 0.185(15) 1 d P B 2
H13D H 0.8946 0.2611 1.0342 0.161 Uiso 0.185(15) 1 calc PR B 2
H13E H 0.8914 0.3265 0.9486 0.161 Uiso 0.185(15) 1 calc PR B 2
H13F H 0.8500 0.1876 0.9383 0.161 Uiso 0.185(15) 1 calc PR B 2
C14' C 0.690(4) 0.358(3) 1.0340(14) 0.101(13) Uani 0.185(15) 1 d P B 2
H14D H 0.5952 0.3685 1.0274 0.151 Uiso 0.185(15) 1 calc PR B 2
H14E H 0.7521 0.4308 1.0256 0.151 Uiso 0.185(15) 1 calc PR B 2
H14F H 0.7266 0.3390 1.0932 0.151 Uiso 0.185(15) 1 calc PR B 2
C15' C 0.610(4) 0.140(3) 0.9846(19) 0.121(17) Uani 0.185(15) 1 d P B 2
H15D H 0.6596 0.1264 1.0432 0.182 Uiso 0.185(15) 1 calc PR B 2
H15E H 0.6091 0.0776 0.9403 0.182 Uiso 0.185(15) 1 calc PR B 2
H15F H 0.5131 0.1404 0.9839 0.182 Uiso 0.185(15) 1 calc PR B 2
C16 C 0.8029(3) 0.4537(2) 0.66628(16) 0.0373(6) Uani 1 1 d . . .
C17 C 0.8121(3) 0.5444(2) 0.73216(17) 0.0498(8) Uani 1 1 d . . .
H17 H 0.7621 0.5396 0.7762 0.060 Uiso 1 1 calc R . .
C18 C 0.9110(3) 0.6445(2) 0.71981(18) 0.0507(8) Uani 1 1 d . . .
H18 H 0.9378 0.7186 0.7542 0.061 Uiso 1 1 calc R . .
C19 C 0.9617(3) 0.6144(2) 0.64794(17) 0.0411(7) Uani 1 1 d . . .
C20 C 1.0573(3) 0.6810(3) 0.60088(19) 0.0471(7) Uani 1 1 d . . .
C21 C 1.1545(3) 0.7994(2) 0.64145(19) 0.0464(7) Uani 1 1 d . . .
C22 C 1.1908(3) 0.8807(3) 0.5847(2) 0.0660(9) Uani 1 1 d . . .
H22 H 1.1496 0.8622 0.5229 0.079 Uiso 1 1 calc R . .
C23 C 1.2878(4) 0.9895(3) 0.6186(3) 0.0810(11) Uani 1 1 d . . .
H23 H 1.3093 1.0445 0.5800 0.097 Uiso 1 1 calc R . .
C24 C 1.3523(4) 1.0156(3) 0.7103(3) 0.0838(12) Uani 1 1 d . . .
H24 H 1.4195 1.0875 0.7331 0.101 Uiso 1 1 calc R . .
C25 C 1.3181(3) 0.9367(3) 0.7670(2) 0.0804(11) Uani 1 1 d . . .
H25 H 1.3610 0.9553 0.8286 0.097 Uiso 1 1 calc R . .
C26 C 1.2191(3) 0.8278(3) 0.7333(2) 0.0646(9) Uani 1 1 d . . .
H26 H 1.1963 0.7740 0.7726 0.078 Uiso 1 1 calc R . .
C27 C 0.6158(3) 0.3031(2) 0.54961(16) 0.0378(7) Uani 1 1 d . . .
C28 C 0.5763(3) 0.3811(3) 0.49192(18) 0.0486(8) Uani 1 1 d . . .
H28 H 0.6095 0.4632 0.5027 0.058 Uiso 1 1 calc R . .
C29 C 0.4773(3) 0.3155(3) 0.41399(18) 0.0503(8) Uani 1 1 d . . .
H29 H 0.4325 0.3460 0.3639 0.060 Uiso 1 1 calc R . .
C30 C 0.4579(3) 0.1967(2) 0.42495(17) 0.0435(7) Uani 1 1 d . . .
C31 C 0.3669(3) 0.0889(3) 0.36869(19) 0.0481(8) Uani 1 1 d . . .
C32 C 0.2804(3) 0.0975(3) 0.27610(18) 0.0499(8) Uani 1 1 d . . .
C33 C 0.3381(3) 0.1686(3) 0.21876(19) 0.0624(9) Uani 1 1 d . . .
H33 H 0.4332 0.2130 0.2375 0.075 Uiso 1 1 calc R . .
C34 C 0.2535(4) 0.1736(3) 0.1329(2) 0.0784(11) Uani 1 1 d . . .
H34 H 0.2926 0.2209 0.0945 0.094 Uiso 1 1 calc R . .
C35 C 0.1129(4) 0.1090(4) 0.1051(2) 0.0846(12) Uani 1 1 d . . .
H35 H 0.0568 0.1130 0.0481 0.102 Uiso 1 1 calc R . .
C36 C 0.0553(4) 0.0387(3) 0.1611(2) 0.0785(11) Uani 1 1 d . . .
H36 H -0.0404 -0.0042 0.1422 0.094 Uiso 1 1 calc R . .
C37 C 0.1385(3) 0.0309(3) 0.2460(2) 0.0663(9) Uani 1 1 d . . .
H37 H 0.0992 -0.0191 0.2829 0.080 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0427(13) 0.0346(15) 0.0435(13) -0.0032(11) 0.0120(11) 0.0020(11)
N2 0.0493(14) 0.0290(14) 0.0455(13) 0.0050(11) 0.0020(11) 0.0027(11)
O1 0.0359(10) 0.0366(12) 0.0595(11) 0.0028(11) 0.0078(9) 0.0069(9)
O2 0.1078(18) 0.0494(15) 0.0682(14) -0.0108(12) 0.0468(14) -0.0085(13)
O3 0.0680(14) 0.0350(13) 0.0663(13) 0.0065(11) -0.0056(11) 0.0021(11)
C1 0.0329(15) 0.0337(17) 0.0466(16) 0.0058(14) 0.0076(13) 0.0065(13)
C2 0.0351(15) 0.0301(16) 0.0404(15) 0.0042(13) 0.0053(13) 0.0019(12)
C3 0.0387(17) 0.0470(19) 0.0502(17) 0.0124(15) 0.0113(14) 0.0081(14)
C4 0.0417(17) 0.055(2) 0.0584(19) 0.0096(16) 0.0147(16) 0.0114(15)
C5 0.057(2) 0.060(2) 0.0513(19) 0.0043(16) 0.0241(16) 0.0113(17)
C6 0.0543(19) 0.054(2) 0.0427(17) 0.0037(15) 0.0084(15) 0.0103(16)
C7 0.0379(16) 0.049(2) 0.0485(17) 0.0018(15) 0.0056(14) 0.0103(14)
C8 0.053(2) 0.096(3) 0.082(3) 0.022(3) 0.029(2) 0.032(2)
C9 0.093(4) 0.125(6) 0.167(11) 0.047(7) 0.040(6) 0.070(4)
C10 0.045(4) 0.173(10) 0.115(6) -0.015(8) -0.004(4) 0.033(6)
C11 0.068(4) 0.188(14) 0.123(6) 0.032(7) 0.054(4) 0.054(6)
C9' 0.053(13) 0.13(3) 0.12(3) 0.012(19) 0.025(15) 0.034(16)
C10' 0.085(17) 0.12(3) 0.13(3) 0.00(2) 0.03(2) 0.052(18)
C11' 0.058(19) 0.14(4) 0.12(2) 0.02(3) 0.008(15) 0.05(2)
C12 0.078(3) 0.099(3) 0.048(2) 0.012(2) 0.0144(19) 0.033(3)
C13 0.126(6) 0.189(12) 0.060(3) 0.040(5) 0.039(4) 0.063(7)
C14 0.125(7) 0.135(6) 0.082(4) 0.049(4) 0.023(4) 0.066(6)
C15 0.112(6) 0.176(9) 0.067(4) 0.007(5) -0.029(4) -0.016(6)
C13' 0.13(2) 0.13(3) 0.040(14) 0.017(16) -0.024(14) 0.04(2)
C14' 0.11(3) 0.12(3) 0.070(15) 0.003(16) 0.008(15) 0.04(2)
C15' 0.14(3) 0.13(3) 0.08(2) 0.03(2) -0.01(2) 0.02(2)
C16 0.0317(15) 0.0351(17) 0.0426(15) 0.0021(14) 0.0099(13) 0.0044(13)
C17 0.0556(19) 0.0394(19) 0.0518(17) -0.0056(15) 0.0232(15) 0.0006(15)
C18 0.0541(19) 0.0372(19) 0.0558(18) -0.0055(15) 0.0172(15) 0.0024(15)
C19 0.0424(16) 0.0304(17) 0.0455(16) 0.0018(14) 0.0104(14) 0.0018(13)
C20 0.0518(18) 0.0390(19) 0.0481(17) 0.0002(16) 0.0165(15) 0.0048(15)
C21 0.0498(18) 0.0351(18) 0.0532(18) 0.0035(16) 0.0195(15) 0.0028(14)
C22 0.080(2) 0.050(2) 0.062(2) 0.0054(18) 0.0263(18) -0.0029(19)
C23 0.101(3) 0.047(2) 0.093(3) 0.011(2) 0.045(2) -0.008(2)
C24 0.083(3) 0.051(2) 0.099(3) -0.009(2) 0.031(2) -0.021(2)
C25 0.077(2) 0.064(3) 0.074(2) -0.004(2) 0.008(2) -0.019(2)
C26 0.063(2) 0.054(2) 0.062(2) 0.0087(18) 0.0096(17) -0.0088(17)
C27 0.0356(15) 0.0322(17) 0.0435(16) 0.0038(14) 0.0101(13) 0.0053(13)
C28 0.0521(18) 0.0327(17) 0.0533(18) 0.0060(15) 0.0049(15) 0.0052(14)
C29 0.0539(18) 0.043(2) 0.0456(17) 0.0091(15) 0.0000(14) 0.0095(15)
C30 0.0437(16) 0.0373(18) 0.0423(16) 0.0056(14) 0.0008(14) 0.0074(14)
C31 0.0448(17) 0.0391(19) 0.0521(18) 0.0007(16) 0.0030(15) 0.0064(15)
C32 0.0541(19) 0.0416(19) 0.0452(17) -0.0046(15) -0.0015(15) 0.0136(15)
C33 0.069(2) 0.064(2) 0.0500(19) 0.0015(18) 0.0067(18) 0.0196(18)
C34 0.098(3) 0.084(3) 0.053(2) 0.007(2) 0.011(2) 0.032(2)
C35 0.099(3) 0.084(3) 0.056(2) -0.008(2) -0.015(2) 0.037(3)
C36 0.066(2) 0.069(3) 0.077(3) -0.014(2) -0.019(2) 0.017(2)
C37 0.064(2) 0.052(2) 0.063(2) -0.0060(17) -0.0101(18) 0.0091(17)
_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 C16 1.352(3) . ?
N1 C19 1.381(3) . ?
N1 H1 0.8600 . ?
N2 C27 1.358(3) . ?
N2 C30 1.380(3) . ?
N2 H2 0.8600 . ?
O1 C1 1.440(3) . ?
O1 H1A 0.8200 . ?
O2 C20 1.231(3) . ?
O3 C31 1.242(3) . ?
C1 C16 1.524(3) . ?
C1 C27 1.532(3) . ?
C1 C2 1.538(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.389(3) . ?
C3 C4 1.401(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 C8 1.546(4) . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(3) . ?
C6 C12 1.540(4) . ?
C7 H7 0.9300 . ?
C8 C11' 1.53(4) . ?
C8 C10' 1.53(3) . ?
C8 C9 1.537(8) . ?
C8 C11 1.538(7) . ?
C8 C10 1.540(9) . ?
C8 C9' 1.54(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9' H9'1 0.9600 . ?
C9' H9'2 0.9600 . ?
C9' H9'3 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 C15 1.514(8) . ?
C12 C15' 1.52(3) . ?
C12 C14 1.530(7) . ?
C12 C14' 1.53(2) . ?
C12 C13' 1.55(3) . ?
C12 C13 1.567(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16 C17 1.388(3) . ?
C17 C18 1.401(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.450(3) . ?
C20 C21 1.489(3) . ?
C21 C22 1.382(3) . ?
C21 C26 1.388(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.372(3) . ?
C28 C29 1.398(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.451(4) . ?
C31 C32 1.500(4) . ?
C32 C33 1.389(4) . ?
C32 C37 1.390(4) . ?
C33 C34 1.398(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.367(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.390(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
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
C16 N1 C19 110.2(2) . . ?
C16 N1 H1 124.9 . . ?
C19 N1 H1 124.9 . . ?
C27 N2 C30 109.8(2) . . ?
C27 N2 H2 125.1 . . ?
C30 N2 H2 125.1 . . ?
C1 O1 H1A 109.5 . . ?
O1 C1 C16 106.26(18) . . ?
O1 C1 C27 110.1(2) . . ?
C16 C1 C27 109.6(2) . . ?
O1 C1 C2 111.7(2) . . ?
C16 C1 C2 107.2(2) . . ?
C27 C1 C2 111.9(2) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 121.1(2) . . ?
C7 C2 C1 119.1(2) . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 117.6(3) . . ?
C5 C4 C8 122.8(3) . . ?
C3 C4 C8 119.6(3) . . ?
C4 C5 C6 122.8(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 C12 120.1(3) . . ?
C5 C6 C12 122.1(3) . . ?
C6 C7 C2 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C11' C8 C10' 110.6(16) . . ?
C11' C8 C9 72.8(17) . . ?
C10' C8 C9 41.9(18) . . ?
C11' C8 C11 130.2(13) . . ?
C10' C8 C11 70.2(17) . . ?
C9 C8 C11 108.1(5) . . ?
C11' C8 C10 39.0(16) . . ?
C10' C8 C10 140.2(12) . . ?
C9 C8 C10 110.5(5) . . ?
C11 C8 C10 107.8(5) . . ?
C11' C8 C9' 110.4(15) . . ?
C10' C8 C9' 110.3(14) . . ?
C9 C8 C9' 142.7(14) . . ?
C11 C8 C9' 40.3(15) . . ?
C10 C8 C9' 74.6(15) . . ?
C11' C8 C4 114.3(12) . . ?
C10' C8 C4 106.8(11) . . ?
C9 C8 C4 107.8(4) . . ?
C11 C8 C4 112.4(4) . . ?
C10 C8 C4 110.2(4) . . ?
C9' C8 C4 104.2(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
C8 C9' H9'1 109.5 . . ?
C8 C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C8 C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
C8 C10' H10D 109.5 . . ?
C8 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C8 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C8 C11' H11D 109.5 . . ?
C8 C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C8 C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C15 C12 C15' 137.7(10) . . ?
C15 C12 C14 111.4(5) . . ?
C15' C12 C14 46.9(17) . . ?
C15 C12 C14' 60.5(13) . . ?
C15' C12 C14' 110.2(16) . . ?
C14 C12 C14' 140.5(10) . . ?
C15 C12 C6 109.8(4) . . ?
C15' C12 C6 111.9(10) . . ?
C14 C12 C6 109.5(3) . . ?
C14' C12 C6 109.3(9) . . ?
C15 C12 C13' 48.1(13) . . ?
C15' C12 C13' 108.5(17) . . ?
C14 C12 C13' 66.1(14) . . ?
C14' C12 C13' 105.7(14) . . ?
C6 C12 C13' 111.1(9) . . ?
C15 C12 C13 108.2(5) . . ?
C15' C12 C13 61.8(16) . . ?
C14 C12 C13 106.4(5) . . ?
C14' C12 C13 51.5(14) . . ?
C6 C12 C13 111.5(3) . . ?
C13' C12 C13 136.6(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
C12 C13' H13D 109.5 . . ?
C12 C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C12 C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C12 C14' H14D 109.5 . . ?
C12 C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C12 C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C12 C15' H15D 109.5 . . ?
C12 C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C12 C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
N1 C16 C17 107.8(2) . . ?
N1 C16 C1 122.1(2) . . ?
C17 C16 C1 130.1(2) . . ?
C16 C17 C18 107.0(2) . . ?
C16 C17 H17 126.5 . . ?
C18 C17 H17 126.5 . . ?
C19 C18 C17 108.3(2) . . ?
C19 C18 H18 125.8 . . ?
C17 C18 H18 125.8 . . ?
C18 C19 N1 106.6(2) . . ?
C18 C19 C20 133.6(3) . . ?
N1 C19 C20 119.6(2) . . ?
O2 C20 C19 120.3(3) . . ?
O2 C20 C21 118.2(2) . . ?
C19 C20 C21 121.4(2) . . ?
C22 C21 C26 118.7(3) . . ?
C22 C21 C20 118.6(2) . . ?
C26 C21 C20 122.5(3) . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 119.5(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 120.1(3) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
N2 C27 C28 107.8(2) . . ?
N2 C27 C1 121.8(2) . . ?
C28 C27 C1 130.2(2) . . ?
C27 C28 C29 108.0(3) . . ?
C27 C28 H28 126.0 . . ?
C29 C28 H28 126.0 . . ?
C30 C29 C28 107.6(2) . . ?
C30 C29 H29 126.2 . . ?
C28 C29 H29 126.2 . . ?
N2 C30 C29 106.8(2) . . ?
N2 C30 C31 120.5(2) . . ?
C29 C30 C31 132.7(3) . . ?
O3 C31 C30 121.6(3) . . ?
O3 C31 C32 119.4(3) . . ?
C30 C31 C32 118.9(3) . . ?
C33 C32 C37 118.8(3) . . ?
C33 C32 C31 122.1(3) . . ?
C37 C32 C31 119.1(3) . . ?
C32 C33 C34 120.1(3) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.2(3) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 120.1(3) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.5(3) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C37 C32 120.2(3) . . ?
C36 C37 H37 119.9 . . ?
C32 C37 H37 119.9 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -153.4(2) . . . . ?
C16 C1 C2 C3 90.7(3) . . . . ?
C27 C1 C2 C3 -29.5(3) . . . . ?
O1 C1 C2 C7 32.4(3) . . . . ?
C16 C1 C2 C7 -83.5(3) . . . . ?
C27 C1 C2 C7 156.3(2) . . . . ?
C7 C2 C3 C4 1.0(4) . . . . ?
C1 C2 C3 C4 -173.2(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 C8 -179.7(3) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C8 C4 C5 C6 179.4(3) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C4 C5 C6 C12 179.4(3) . . . . ?
C5 C6 C7 C2 1.6(4) . . . . ?
C12 C6 C7 C2 -178.1(3) . . . . ?
C3 C2 C7 C6 -2.0(4) . . . . ?
C1 C2 C7 C6 172.3(2) . . . . ?
C5 C4 C8 C11' -172(2) . . . . ?
C3 C4 C8 C11' 8(2) . . . . ?
C5 C4 C8 C10' 65(2) . . . . ?
C3 C4 C8 C10' -115(2) . . . . ?
C5 C4 C8 C9 109.4(7) . . . . ?
C3 C4 C8 C9 -70.6(8) . . . . ?
C5 C4 C8 C11 -9.6(8) . . . . ?
C3 C4 C8 C11 170.4(7) . . . . ?
C5 C4 C8 C10 -129.8(8) . . . . ?
C3 C4 C8 C10 50.2(8) . . . . ?
C5 C4 C8 C9' -51(2) . . . . ?
C3 C4 C8 C9' 129(2) . . . . ?
C7 C6 C12 C15 61.3(6) . . . . ?
C5 C6 C12 C15 -118.4(6) . . . . ?
C7 C6 C12 C15' -112(2) . . . . ?
C5 C6 C12 C15' 69(2) . . . . ?
C7 C6 C12 C14 -61.3(5) . . . . ?
C5 C6 C12 C14 119.0(5) . . . . ?
C7 C6 C12 C14' 126.0(17) . . . . ?
C5 C6 C12 C14' -53.7(18) . . . . ?
C7 C6 C12 C13' 9.8(18) . . . . ?
C5 C6 C12 C13' -169.9(17) . . . . ?
C7 C6 C12 C13 -178.7(5) . . . . ?
C5 C6 C12 C13 1.5(7) . . . . ?
C19 N1 C16 C17 1.4(3) . . . . ?
C19 N1 C16 C1 -179.9(2) . . . . ?
O1 C1 C16 N1 62.3(3) . . . . ?
C27 C1 C16 N1 -56.6(3) . . . . ?
C2 C1 C16 N1 -178.2(2) . . . . ?
O1 C1 C16 C17 -119.3(3) . . . . ?
C27 C1 C16 C17 121.8(3) . . . . ?
C2 C1 C16 C17 0.2(4) . . . . ?
N1 C16 C17 C18 -0.5(3) . . . . ?
C1 C16 C17 C18 -179.1(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 N1 1.3(3) . . . . ?
C17 C18 C19 C20 175.7(3) . . . . ?
C16 N1 C19 C18 -1.7(3) . . . . ?
C16 N1 C19 C20 -177.0(2) . . . . ?
C18 C19 C20 O2 -163.6(3) . . . . ?
N1 C19 C20 O2 10.2(4) . . . . ?
C18 C19 C20 C21 17.2(5) . . . . ?
N1 C19 C20 C21 -169.0(2) . . . . ?
O2 C20 C21 C22 30.5(4) . . . . ?
C19 C20 C21 C22 -150.3(3) . . . . ?
O2 C20 C21 C26 -144.2(3) . . . . ?
C19 C20 C21 C26 35.1(4) . . . . ?
C26 C21 C22 C23 -1.1(5) . . . . ?
C20 C21 C22 C23 -176.0(3) . . . . ?
C21 C22 C23 C24 1.9(5) . . . . ?
C22 C23 C24 C25 -1.8(6) . . . . ?
C23 C24 C25 C26 0.9(6) . . . . ?
C22 C21 C26 C25 0.2(5) . . . . ?
C20 C21 C26 C25 174.9(3) . . . . ?
C24 C25 C26 C21 -0.1(5) . . . . ?
C30 N2 C27 C28 -0.2(3) . . . . ?
C30 N2 C27 C1 175.2(2) . . . . ?
O1 C1 C27 N2 50.6(3) . . . . ?
C16 C1 C27 N2 167.1(2) . . . . ?
C2 C1 C27 N2 -74.2(3) . . . . ?
O1 C1 C27 C28 -135.1(3) . . . . ?
C16 C1 C27 C28 -18.6(4) . . . . ?
C2 C1 C27 C28 100.1(3) . . . . ?
N2 C27 C28 C29 0.3(3) . . . . ?
C1 C27 C28 C29 -174.6(2) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
C27 N2 C30 C29 0.0(3) . . . . ?
C27 N2 C30 C31 -178.3(2) . . . . ?
C28 C29 C30 N2 0.2(3) . . . . ?
C28 C29 C30 C31 178.1(3) . . . . ?
N2 C30 C31 O3 6.4(4) . . . . ?
C29 C30 C31 O3 -171.3(3) . . . . ?
N2 C30 C31 C32 -176.9(2) . . . . ?
C29 C30 C31 C32 5.4(5) . . . . ?
O3 C31 C32 C33 -139.3(3) . . . . ?
C30 C31 C32 C33 43.9(4) . . . . ?
O3 C31 C32 C37 39.7(4) . . . . ?
C30 C31 C32 C37 -137.1(3) . . . . ?
C37 C32 C33 C34 0.8(4) . . . . ?
C31 C32 C33 C34 179.8(3) . . . . ?
C32 C33 C34 C35 0.4(5) . . . . ?
C33 C34 C35 C36 -0.4(5) . . . . ?
C34 C35 C36 C37 -0.8(6) . . . . ?
C35 C36 C37 C32 2.0(5) . . . . ?
C33 C32 C37 C36 -2.0(5) . . . . ?
C31 C32 C37 C36 178.9(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.041